Ethanol → HCID 59201362, compound

Participants

Reaction Conditions

Reaction Steps

tert-butyl (2R,3S)-3-cyclohexyl-2-(1,3-dioxoisoindolin-2-yl)-3-hydroxypropyl(methyl)carbamate (500 mg, 1.20 mmol) was dissolved into a minimal volume of EtOH (12 mL) and hydrazine monohydrate (85% in EtOH, 0.35 mL, 6.00 mmol) was added. The solution was heated at 55° C. for 45 min and then the reaction temperature was raised to reflux for 2 h. A white solid formed. The reaction was cooled to rt, Et2O (50 mL) was added and the reaction was filtered. The filtrate was stripped and the residue was stirred in Et2O (15 mL) for 1 h and filtered. The filtrate was stripped to afford tert-butyl (2R,3S)-2-amino-3-cyclohexyl-3-hydroxypropyl(methyl)carbamate (300 mg, yield 87%), which was pure enough to use directly in the next step. MS (E/Z): 287 (M+H+).

Provenance & Evidence