ChemicalBook > CAS DataBase List > 1-tert-Butyl 2-methyl (2R)-4-oxopyrrolidine-1,2-dicarboxylate

1-tert-Butyl 2-methyl (2R)-4-oxopyrrolidine-1,2-dicarboxylate

Product Name: 1-tert-Butyl 2-methyl (2R)-4-oxopyrrolidine-1,2-dicarboxylate
CAS No.: 256487-77-1
Chemical Name: 1-tert-Butyl 2-methyl (2R)-4-oxopyrrolidine-1,2-dicarboxylate
Synonyms: 1-(tert-Butyl) 2-methyl (R)-4-oxopyrrolidine-1,2-dicarboxylate;Boc-4-OXO-D-Pro-Ome;N-Boc-4-oxo-L-Pro.Ome;N-Boc-4-oxo-L-proline m;Methyl N-Boc-4-keto-D-prolinate;Boc-4-oxo-D-proline Methyl ester;(2R)-N-Boc-4-oxo-D-proline methyl ester;N-Boc-4- oxygen -D- proline methyl ester;(R)-N-Boc-2-Methoxycarbonyl-4-pyrrolidone;N-Boc-4-oxo-L-proline methyl ester USP/EP/BP
CBNumber: CB72469884
Molecular Formula: C11H17NO5
Formula Weight: 243.26
MOL File: 256487-77-1.mol

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1-tert-Butyl 2-methyl (2R)-4-oxopyrrolidine-1,2-dicarboxylate Property

Boiling point:: 333.1±42.0 °C(Predicted)
Density: 1.209
storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
pka: -3.86±0.40(Predicted)
Appearance: Off-white to yellow Solid-Liquid Mixture
InChI: InChI=1S/C11H17NO5/c1-11(2,3)17-10(15)12-6-7(13)5-8(12)9(14)16-4/h8H,5-6H2,1-4H3/t8-/m1/s1
InChIKey: UPBHYYJZVWZCOZ-MRVPVSSYSA-N
SMILES: N1(C(OC(C)(C)C)=O)CC(=O)C[C@@H]1C(OC)=O

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Safety

HazardClass: IRRITANT
HS Code: 2933998090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

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N-Bromosuccinimide Price

TRC

Product number: B661535
Product name: N-Boc-4-oxo-D-ProlineMethylEster
Packaging: 100mg
Price: $50
Updated: 2021/12/16

Activate Scientific

Product number: AS72006
Product name: (R)-1-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate
Purity: 97+% ee
Packaging: 1g
Price: $65
Updated: 2021/12/16

Matrix Scientific

Product number: 057296
Product name: (R)-1-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate
Purity: 95%
Packaging: 1g
Price: $70
Updated: 2021/12/16

Matrix Scientific

Product number: 057296
Product name: (R)-1-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate
Purity: 95%
Packaging: 250mg
Price: $35
Updated: 2021/12/16

SynQuest Laboratories

Product number: 4H58-1-9P
Product name: (R)-1-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate
Packaging: 1g
Price: $150
Updated: 2021/12/16

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1-tert-Butyl 2-methyl (2R)-4-oxopyrrolidine-1,2-dicarboxylate Chemical Properties,Usage,Production

Uses

N-Boc-4-oxo-D-Proline methyl ester is a useful chemical reagent.

Synthesis

114676-69-6

256487-77-1

General procedure for the synthesis of (R)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylates from methyl (2R,4R)-1-Boc-4-hydroxypyrrolidine-2-carboxylate: Step 1: Oxidation reaction Pyridinium dichromate (9.97 g, 26.5 mmol) was dissolved in dichloromethane (60 mL) at room temperature and slowly added to a dichloromethane solution of methyl (2R,4R)-1-Boc-4-hydroxypyrrolidine-2-carboxylate (5.00 g, 20.39 mmol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, diatomaceous earth (5 g) was added and stirring was continued for 40 min, followed by filtration. The filter cake was washed with dichloromethane (50 mL x 3). The filtrates were combined, concentrated to dryness under reduced pressure, added toluene (40 mL) and concentrated again to give about 6.5 g of brown slurry-like crude product. Purification step The crude product was purified by fast silica gel column chromatography (120 g silica gel column, eluent EtOAc/hexane, gradient 0 to 100%, flow rate 85 mL/min) to afford 4.18 g (84% yield) of (R)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate as a white solid. Product characterization LCMS (condition A): m/z 144 (M-Boc)-ve. 1H NMR (400 MHz, CDCl3) δ ppm: 4.44-4.89 (1H, m), 3.84-3.96 (2H, m), 3.77 (3H, s), 2.81-3.10 (1H, m), 2.59 (1H, dd, J = 18.93, 1.76 Hz), 1.52 (9H, s).

References

[1] Patent: WO2012/125887, 2012, A1. Location in patent: Page/Page column 74-75
[2] Patent: WO2012/125886, 2012, A1. Location in patent: Page/Page column 85
[3] Patent: WO2015/94902, 2015, A1. Location in patent: Page/Page column 20; 21
[4] Journal of Medicinal Chemistry, 1999, vol. 42, # 26, p. 5426 - 5436
[5] Patent: TW2017/8221, 2017, A. Location in patent: Page/Page column 41; 42

1-tert-Butyl 2-methyl (2R)-4-oxopyrrolidine-1,2-dicarboxylate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 1-tert-Butyl 2-methyl (2R)-4-oxopyrrolidine-1,2-dicarboxylate manufacturers

Sichuan HongRi Pharma-Tech Co.,Ltd

Product: N-Boc-4-oxo-L-proline methyl ester 256487-77-1
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1T
Release date: 2023-11-21

Career Henan Chemical Co

Product: N-Boc-4-oxo-L-proline methyl ester 256487-77-1
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 200kg
Release date: 2019-12-31

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256487-77-1