(R)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate

Product Name: (R)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate
CAS No.: 1306763-30-3
Chemical Name: (R)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate
Synonyms: Ozanimod intermediate 1;(R)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate;tert-butyl (R)-(4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate;TERT-BUTYL N-[(1R)-4-CYANO-2,3-DIHYDRO-1H-INDEN-1-YL]CARBAMATE;( S )- tert - butyl (4- cyano -2,3- dihydro -1H- inden -1-y1) carbamate;Carbamic acid, N-[(1R)-4-cyano-2,3-dihydro-1H-inden-1-yl]-, 1,1-dimethylethyl ester
CBNumber: CB93051606
Molecular Formula: C15H18N2O2
Formula Weight: 258.32
MOL File: 1306763-30-3.mol

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(R)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate Property

Boiling point:: 411.9±44.0 °C(Predicted)
Density: 1.15±0.1 g/cm3(Predicted)
storage temp.: 2-8°C
pka: 11.86±0.20(Predicted)

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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

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

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

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N-Bromosuccinimide Price

TRC

Product number: B809580
Product name: (R)-tert-Butyl(4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate
Packaging: 100mg
Price: $220
Updated: 2021/12/16

AK Scientific

Product number: 1296DJ
Product name: (R)-Tert-Butyl(4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate
Packaging: 1g
Price: $300
Updated: 2021/12/16

AK Scientific

Product number: 1296DJ
Product name: (R)-Tert-Butyl(4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate
Packaging: 100mg
Price: $126
Updated: 2021/12/16

Ambeed

Product number: A185292
Product name: (R)-tert-Butyl(4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate
Purity: 97%
Packaging: 1g
Price: $178
Updated: 2021/12/16

Ambeed

Product number: A185292
Product name: (R)-tert-Butyl(4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate
Purity: 97%
Packaging: 100mg
Price: $49
Updated: 2021/12/16

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(R)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate Chemical Properties,Usage,Production

Uses

(R)-tert-Butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate is a useful reagent in the preparation of oxadiazoles as sphingosine 1 phosphate receptor modulators useful in the treatment of S1P1-associated diseases.

Synthesis

24424-99-5

1306763-29-0

1306763-30-3

At 0 °C, (R)-1-amino-2,3-dihydro-1H-indene-4-carbonitrile hydrochloride (INT-50, 11.6 g, 59.6 mmol) was dissolved in dichloromethane (DCM, 100 mL) and triethylamine (TEA, 12.0 mL, 131.0 mmol) was added. Subsequently, a solution of di-tert-butyl dicarbonate (Boc anhydride, 14.3 g, 65.6 mmol) in DCM (30 mL) was slowly added to the reaction system. The reaction mixture was stirred at room temperature for 1.5 hours. Upon completion of the reaction, the reaction mixture was washed with brine and the organic layer was dried over anhydrous magnesium sulfate (MgSO4) and filtered. Additional DCM was added to the filtrate to a total volume of 250 mL and activated carbon (Norit, 4.5 g) was added. The mixture was refluxed for 15 minutes and then filtered through a diatomaceous earth/silica pad while hot. The filtrate was concentrated and recrystallized by ethyl acetate (EA, 50 mL) and hexane (150 mL) to afford 12.93 g (84% yield) of tert-butyl (R)-(4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate (INT-52) as an off-white solid.Calculated values for LCMS-ESI (m/z): C15H18N2O2 were 258.3; measured value was 281.1 [M+Na]+, retention time (tR) = 3.45 min. Elemental analysis results (C15H18N2O2): calculated C=69.74%, H=7.02%, N=10.84%; measured C=69.98%, H=7.14%, N=10.89%.1H NMR (400MHz, CDCl3) δ: 7.64-7.49 (m, 2H), 7.34 (dt, J=7.7, 3.8Hz, 1H). 3.8 Hz, 1H), 5.36-5.20 (m, 1H), 4.78 (d, J=6.8 Hz, 1H), 3.20 (ddd, J=16.9,8.9,3.3 Hz, 1H), 3.02 (dt, J=25.4,8.4 Hz, 1H), 2.82-2.53 (m, 1H), 1.88 (dq, J=13.2 ,8.6Hz, 1H), 1.55-1.44 (m, 9H).13C NMR (101MHz, DMSO) δ: 155.52, 146.68, 146.32, 130.89, 128.70, 127.63, 117.51, 107.76, 77.98, 55.09, 31.88, 29.11. 28.19. Chiral HPLC analysis: tert-butyl (R)-4-cyano-2,3-dihydro-1H-inden-1-ylcarbamate showed an enantiomeric excess (ee) of >99.9% and a retention time (tR) = 19.36 min, using a hexane solution of 2.5% ethanol as eluent.

References

[1] Patent: WO2011/60389, 2011, A1. Location in patent: Page/Page column 92-93
[2] Patent: WO2015/66515, 2015, A1. Location in patent: Page/Page column 78-79
[3] Patent: WO2018/64356, 2018, A1. Location in patent: Page/Page column 57

(R)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate Preparation Products And Raw materials

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(R)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate Suppliers

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Shanghai Boyle Chemical Co., Ltd.

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View Lastest Price from (R)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate manufacturers

Career Henan Chemical Co

Product: (S)-tert-butyl(4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate 1306763-30-3
Price: US $1.00/g
Min. Order: 1g
Purity: 99%
Supply Ability: g/kg/T
Release date: 2019-12-18

1306763-30-3, (R)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamateRelated Search:

(S)-1-amino-2,3-dihydro-1H-indene-4-carbonitrile hydrochloride 3-CYANO-4-ISOPROPOXYBENZOIC ACID 2,3-dihydro-1-oxo-1H-indene-4-carbonitrile tert-Butyl (2-chloro-3-Methylpyridin-4-yl)carbaMate Boc-(S)-1-(4-bromophenyl)-2-hydroxyethylamine Tert-butyl3-hydroxycyclopentylcarbamate TERT-BUTYL N-[(1R)-1-CYCLOPROPYL-2-HYDROXYETHYL]CARBAMATE 2-(Boc-amino)-2-cyclopropylethanol Carbamic acid, N-(4-cyano-2,3-dihydro-1H-inden-1-yl)-, 1,1-dimethylethyl ester Carbamic acid, N-[(1S)-1-cyclopropyl-2-hydroxyethyl]-, 1,1-dimethylethyl ester tert-butyl(1-(5-bromo-2-fluorophenyl)-2-HYDROxyethyl)carbamate

Ozanimod intermediate 1

TERT-BUTYL N-[(1R)-4-CYANO-2,3-DIHYDRO-1H-INDEN-1-YL]CARBAMATE

Carbamic acid, N-[(1R)-4-cyano-2,3-dihydro-1H-inden-1-yl]-, 1,1-dimethylethyl ester

( S )- tert - butyl (4- cyano -2,3- dihydro -1H- inden -1-y1) carbamate

tert-butyl (R)-(4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate

(R)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate

1306763-30-3