ChemicalBook CAS DataBase List tert-Butyl 3-aminobenzylcarbamate

tert-Butyl 3-aminobenzylcarbamate synthesis

7synthesis methods

Product Name:tert-Butyl 3-aminobenzylcarbamate
CAS Number:147291-66-5
Molecular formula:C12H18N2O2
Molecular Weight:222.28

147291-65-4

147291-66-5

Step 2: Synthesis of tert-butyl 3-aminobenzylcarbamate (3); To a solution of tert-butyl 3-nitrobenzylcarbamate (2, 0.69 g, 2.73 mmol) in ethanol (20 mL) was added 10% Pd-C (50 mg), and the resulting mixture was stirred for 30 min at room temperature under hydrogen atmosphere. The reaction progress was monitored by thin layer chromatography (TLC). After completion of the reaction, the reaction mixture was filtered through diatomaceous earth and washed with ethanol. Ethanol was evaporated from the filtrate under reduced pressure to give tert-butyl 3-aminobenzylcarbamate (3, 0.6 g, 98%). NMR hydrogen spectrum (400 MHz, CDCl3): δ 7.22 (s, 1H), 7.10-7.00 (t, 1H), 6.70-6.60 (d, 1H), 6.60-6.50 (m, 1H), 4.20 (bs, 2H), 1.40 (s, 9H).

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Yield: 98%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in ethanol at 20; for 0.5 h;

Steps:

9.2
Step 2: Synthesis of tert-butyl 3-aminobenzylcarbamate (3); To a solution of tert-butyl 3-nitrobenzylcarbamate (2, 0.69 g, 2.73 mmol) in ethanol (20 mL) was added 10% Pd-C (50 mg), and the resultant mixture was stirred at room temperature under hydrogen atmosphere for 30 min. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite and washed with ethanol. The ethanol was evaporated from the filtrate under reduced pressure to afford tert-butyl 3-aminobenzylcarbamate (3, 0.6 g, 98 %). NMR (400 MHz, CDCI₃): δ 7.22 (s, 1 H), 7.10-7.00 (t, 1 H), 6.70-6.60 (d, 1 H), 6.60-6.50 (m, l H), 4.20 (bs, 2H), 1.40 (s, 9H).

References:

GATEKEEPER PHARMACEUTICALS, INC.;GRAY, Nathanael, S.;ZHOU, Wenjun WO2011/140338, 2011, A1 Location in patent:Page/Page column 60-61

24424-99-5 Synthesis