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

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

4synthesis methods

Product Name:(R)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate
CAS Number:1306763-31-4
Molecular formula:C15H18N2O2
Molecular Weight:258.32

24424-99-5 Synthesis

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(S)-1-amino-2,3-dihydro-1H-indene-4-carbonitrile hydrochloride

1306763-57-4
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(R)-tert-butyl (4-cyano-2,3-dihydro-1H-inden-1-yl)carbamate

1306763-31-4
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Yield:1306763-31-4 92.71%

Reaction Conditions:

with triethylamine in dichloromethane at 5 - 20; for 2 h;

Steps:

5 Example 5: Preparation of (S)-tert-butyl 4-cyano-2,3-dihydro-lH-inden-l- ylcarbamate, a compound of Formula 7:

To a stirred solution of 30.0 gm of amine.HCl (Formula 6) (0.154 moles) and 300.0 of dichloromethane, 31.2 gm of triethyl amine (0.308 moles, 2.0 eq.)was added at 5-15°C. 43.47 gm of Boc anhydride (85%) (0.169 moles, 1.1 eq.) was added and warmed to ambient temperature. The reaction mass was stirred for 2.0hrs. After completion, the reaction mass was washed with water and brine solution. The organic layer was concentrated, cooled and stirred with hexane. The product was filtered, washed with hexane and dried to obtain off-white solid of Formula 7(36.9 gm, 92.71% yield) with HPLC Purity 96.93% & SOR -122° (c=l in CHC1₃at 25°C).MR: 129.7-132.1°C; IR (KBr, cm^"1): 3364, 2979, 2225, 1677, 1514, 1169; 1H- NMR(CDC1₃): δ 7.56-7.50 (m, 2H), 7.33-7.29 (t, 1H, J=7.64Hz), 5.25-5.23 (m, 1H), 4.76-4.74 (d, 1H, J=6.24Hz) , 3.20-3.14 (m, 1H), 2.99 (m, 1H), 2.68-2.64 (m, 1H), 1.89-1.83 (m, 1H), 1.49 (s, 9H);¹³C-NMR(CDC1₃): 155.55, 147.03, 145.44, 131.34, 128.72, 127.56, 117.50, 109.01, 79.84, 55.79, 33.51, 29.62, 28.37(3C); MS (m/z): 259.0 [M+l]⁺, 203.1 [M-C(CH₃)₃]⁺.

References:

WO2019/58290,2019,A1 Location in patent:Page/Page column 21

24424-99-5 Synthesis

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