Acetic Acid → HCID 58981716, compound

Participants

Reaction Steps

To a solution of 5.25 g (30.4 mmol) of tert-butyl (1S)-1-methyl-2-oxoethylcarbamate in 30 mL of methanol at 0° C. was added 2.18 g (33.4 mmol) of potassium cyanide, followed by 1.74 mL (33.4 mmol) of acetic acid. The reaction mixture was warmed to room temperature, left stirring for 16 h, and then filtered and concentrated under vacuum. The residue was dissolved in 80 mL of acetic acid, and 0.8 g of platinum oxide on carbon was added. The reaction mixture was then stirred under 40 psi of hydrogen for 4 h. The catalyst was filtered off over celite, and the filtrate was washed with methanol and concentrated to afford 3.06 g (49%) of tert-butyl (1S,2S)-3-amino-2-hydroxy-1-methylpropylcarbamate & tert-butyl (1S,2R)-3-amino-2-hydroxy-1-methylpropylcarbamate. 1H-NMR (300 MHz, DMSO-d6): δ 6.74, 6.59 (d, J=8 Hz, 1H), 3.61–3.38 (m, 3H), 2.80 (m, 1H), 2.51 (m, 2H), 1.45 (br s, 1H), 1.38 (s, 9H), 0.97 (m, 3H). GC-MS m/z 205 (M+H).

Provenance & Evidence