Diethyl Ether → HCID 59382987, compound

Participants

Reaction Conditions

Reaction Steps

2-((1S,2R)-1-cyclopentyl-1-hydroxy-3-(N-methyl-N-(t-butoxycarbonyl)amino)propan-2-yl)isoindoline-1,3-dione (0.7961 mg, 2.0 mmol) was dissolved in a minimal volume of EtOH (20 mL) and hydrazine monohydrate (0.5 mL, 10.3 mmol) was added. The solution was heated at 55° C. for 45 min and at reflux for 2 h. A white solid (precipitation of the hydrazone) resulted and the reaction was cooled to rt. Ether (50 mL) was added and the reaction was filtered through #1 Whatman filter paper. The filtrate was stripped and the residue was stirred in ether (15 mL) for 1 h, filtered, and stripped to give tert-butyl (2R,3S)-2-amino-3-cyclopentyl-3-hydroxypropyl-methylcarbamate (199.7 mg, 36%). LC-MS (3 min) tR=1.10 min, m/z=272 (M+).

Provenance & Evidence