Water → HCID 57544762, compound

Participants

Reaction Conditions

Reaction Steps

A 1 M solution of LiAlH4 in THF (35 mL, 35.0 mmol) was added to a solution of (S)-tert-butyl 3-cyclohexyl-1-(dimethylamino)-1-oxopropan-2-ylcarbamate (3.85 g, 12.9 mmol) in THF at −78° C. at a rate to maintain the temperature below −60° C. The reaction was permitted to warm to 25° C. and conversion to product was monitored by LC-MS. After 6 h, the reaction was cooled to 0° C., and H2O (3.0 mL) was added dropwise, followed by 1 N aq NaOH (3.0 mL), maintaining the temperature below 10° C. Ether (100 mL) and Celite (10 g) were added to the heterogenous mixture, stirred for 30 minutes and filtered through a pad of Celite. The solvent was removed and the residue was separated on 12 g of SiO2 with an eluent gradient from hexanes to 30% MeOH in EA. Appropriate fractions were combined and the solvent was removed to afford (S)-tert-butyl 1-cyclohexyl-3-(dimethylamino)propan-2-ylcarbamate (0.26 g, 7%) as a white solid. MS ESI+ve m/z 285 (M+Na)+.

Provenance & Evidence