Carbamic acid, N-[(1S)-2-azido-1-methylethyl]-, methyl ester → (S)-methyl 1-aminopropan-2-ylcarbamate

To a solution of Intermediate (S)-methyl 1-azidopropan-2-ylcarbamate (2.86 g, 18.2 mmol) in ethyl acetate (200 ml) was added 10% palladium on carbon (wet, 286 mg). The flask was degassed and refilled with hydrogen gas (balloon, 1 atmosphere), and the mixture was stirred at rt for 16 hours. The reaction mixture was filtered through a pad of celite and washed with ethyl acetate. The filtrate was concentrated to give crude (S)-methyl 1-aminopropan-2-ylcarbamate, which was used without further purification. 1H NMR 400 MHz (CDCl3) δ 4.79 (s, 1H), 3.71-3.65 (m, 1H), 3.66 (s, 3H), 2.75 (dd, 1H), 2.65 (dd, 1H), 1.14 (d, 3H); MS m/z 133.1 (M+1).

1. customThe flask was degassed
2. additionrefilled with hydrogen gas (balloon, 1 atmosphere)
3. filtrationThe reaction mixture was filtered through a pad of celite
4. washwashed with ethyl acetate
5. concentrationThe filtrate was concentrated

ORD record

ord-a44d69ac687a408792fd80ca1f22afba

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09314464B2