ChemicalBook > CAS DataBase List > (S)-(-)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE

(S)-(-)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE

Uses

Product Name: (S)-(-)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE
CAS No.: 131852-53-4
Chemical Name: (S)-(-)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE
Synonyms: (s)-n-benzyl-3-boc-amino Pyrrolidine;(S)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE;(S)-1-BENZYL-3-N-BOC-AMINO-PYRROLIDINE;(S)-(-)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE;TERT-BUTYL(S)-1-BENZYLPYRROLIDIN-3-YLCARBAMATE;(S)-Tert-butyl 1-benzylpyrrolidin-3-ylcarbamate;(S)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE;(1-Benzyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester;(S)-(1-Benzyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester;Carbamic acid, N-[(3S)-1-(phenylmethyl)-3-pyrrolidinyl]-, 1,1-dimethylethyl ester
CBNumber: CB6246620
Molecular Formula: C16H24N2O2
Formula Weight: 276.37
MOL File: 131852-53-4.mol

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(S)-(-)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE Property

Melting point:: 77-81 °C(lit.)
Boiling point:: 385.1±31.0 °C(Predicted)
Density: 1.08±0.1 g/cm3(Predicted)
storage temp.: 2-8°C
form: solid
pka: 12.31±0.20(Predicted)
optical activity: [α]20/D -6°, c =1% in chloroform

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Chem-Impex

Product number: 41588
Product name: (S)-(-)-1-Benzyl-3-(Boc-amino)pyrrolidine,97%
Purity: 97%
Packaging: 1G
Price: $81.76
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FB149389
Product name: (S)-(-)-1-Benzyl-3-(boc-amino)pyrrolidine
Packaging: 1g
Price: $97
Updated: 2021/12/16

AK Scientific

Product number: 0745CS
Product name: (S)-Tert-Butyl(1-benzylpyrrolidin-3-yl)carbamate
Packaging: 500mg
Price: $124
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FB149389
Product name: (S)-(-)-1-Benzyl-3-(boc-amino)pyrrolidine
Packaging: 2g
Price: $168
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FB149389
Product name: (S)-(-)-1-Benzyl-3-(boc-amino)pyrrolidine
Packaging: 500mg
Price: $55
Updated: 2021/12/16

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(S)-(-)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE Chemical Properties,Usage,Production

Uses

(S)-(-)-1-benzyl-3-(tert-butoxycarbonylamino)pyrrolidine is mainly used in organic synthesis and chemical and pharmaceutical research and development.

Synthesis

24424-99-5

114715-38-7

131852-53-4

To a 500 mL four-necked flask equipped with a stirrer, thermometer, Dimroth condenser tube, and constant-pressure dropping funnel was added 17.6 g (0.1 mol, optical purity 99.5% ee) of (S)-3-amino-1-benzylpyrrolidine. Subsequently, 158.7 g of water and 0.2 g of cationic DS (manufactured by Sanyo Chemical Industries, Ltd.) were added, and the pH of the mixture was adjusted to 11.0 ± 0.5 using a 48% aqueous sodium hydroxide solution.The mixture was stirred at 50 to 60 °C while 26.2 g (0.12 mol) of di-tert-butyl dicarbonate (abbreviated as DiBoc), the titration process lasted about 2 hours. During this time, the pH of the reaction solution was maintained at 11.0 ± 0.5 with 48% aqueous sodium hydroxide.After the dropwise addition, stirring was continued for 1 h. The reaction solution was then cooled to room temperature and the crystals were separated by filtration. The resulting crystals were dried under vacuum at 50 °C to afford 26.0 g of (S)-1-benzyl-3-(tert-butoxycarbonylamino)pyrrolidine in 94.1% yield, 99.1% chemical purity, and 99.5% ee optical purity. Using the same apparatus as above, 26.0 g (optical purity 99.5% ee) of (S)-1-benzyl-3-(tert-butoxycarbonylamino)pyrrolidine, 120 g of water, and 2.6 g of 5% Pd/C (PE-type, 55.27% water content, produced by NE Chemcat Corp.) were added and stirred at a reaction temperature of 40 °C for 10 h under hydrogen atmosphere. The reaction solution was analyzed by GC and it was confirmed that the feedstock peak disappeared and only 3-(tert-butoxycarbonylamino)pyrrolidine and toluene were detected. Upon completion of the reaction, the Pd/C was removed by filtration and the filtrate was concentrated using a rotary evaporator to 30 g. Subsequently, the concentrate was mixed with toluene and concentrated again to 20 g. Water was removed by azeotropic distillation. Under stirring, 25 g of hexane was slowly added to the concentrate to precipitate crystals and stirring was continued for 2 hours in an ice bath. The precipitated crystals were separated by filtration and dried under vacuum to give a final 15.4 g of (S)-3-(tert-butoxycarbonylamino)pyrrolidine in 87.4% yield, 99.5% chemical purity, 99.5% optical purity ee, and 0.4% moisture content.

References

[1] Patent: EP1640364, 2006, A1. Location in patent: Page/Page column 10-11
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 11, p. 1815 - 1826

(S)-(-)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE Preparation Products And Raw materials

Raw materials

Preparation Products

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(S)-(-)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE Suppliers

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View Lastest Price from (S)-(-)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE manufacturers

Career Henan Chemical Co

Product: (S)-(-)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE 131852-53-4
Price: US $0.01/KG
Min. Order: 500g
Purity: 98%; 99%
Supply Ability: 500g；1kg； 10kg; 25kg
Release date: 2020-01-08

131852-53-4, (S)-(-)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINERelated Search:

(S)-1-BENZYL-3-N-BOC-AMINOMETHYLPYRROLIDINE (R)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE,(R)-(+)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE,(R)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE,(R)-(+)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE 1-Benzyl-3-(Boc-amino)pyrrolidine,1-Benzyl-3-(Boc-amino)pyrrolidine 1-BENZYL-3-BOC-AMINO-PYRROLIDINE-3-CARBOXYLIC ACID,1-BENZYL-3-BOC-AMINO-PYRROLIDINE-3-CARBOXYLIC ACID (S)-(+)-1-Benzyl-3-aminopyrrolidine 1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE (S)-(-)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE (3-BENZYLAMINO-1-METHYL-PROPYL)-CARBAMIC ACID TERT-BUTYL ESTER 3-(DIETHYLAMINO)PYRROLIDINE (S)-3-(Boc-amino)pyrrolidine Trans (+/-)-Tert-Butyl 1-Benzyl-4-(4-Chlorophenyl) Pyrrolidin-3-Ylcarbamate (R,R)-N-BENZYL-3,4-TRANS-(N-BOC)-DIAMINOPYRROLIDINE

TERT-BUTYL(S)-1-BENZYLPYRROLIDIN-3-YLCARBAMATE

(S)-1-BENZYL-3-(TERT-BUTOXYCARBONYLAMINO)PYRROLIDINE

(S)-(-)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE

(S)-1-BENZYL-3-(BOC-AMINO)PYRROLIDINE

(s)-n-benzyl-3-boc-amino Pyrrolidine

(S)-1-BENZYL-3-N-BOC-AMINO-PYRROLIDINE

(S)-Tert-butyl 1-benzylpyrrolidin-3-ylcarbamate

(1-Benzyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester

(S)-(1-Benzyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester

Carbamic acid, N-[(3S)-1-(phenylmethyl)-3-pyrrolidinyl]-, 1,1-dimethylethyl ester

131852-53-4