Sodium borohydride → HCID 21902127, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:15][CH:16]([CH3:21])[C:17]([F:20])([F:19])[F:18])[C:10](OCC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[F:18][C:17]([F:19])([F:20])[CH:16]([CH3:21])[CH2:15][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH2:10][OH:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To the solution of ethyl 2-((tert-butoxycarbonyl)amino)-5,5,5-trifluoro-4-methylpentanoate (500 mg, 1.596 mmol) in ethanol (2 mL) at 0° C. was added NaBH4 (604 mg, 15.96 mmol). The reaction mixture was allowed to stir at RT for 16 h. The reaction mixture was quenched with aqueous ammonia. The solution was filter through a glass funnel and the resulting filtrate was concentrated to afford the tert-butyl (5,5,5-trifluoro-1-hydroxy-4-methylpentan-2-yl)carbamate (400 mg, 1.475 mmol, 92% crude yield) as a colorless gummy semisolid material. The material was carried on without further purification. LC/MS (ESI) m/e 172.1 [(M+H)+, calcd for C6H13F3NO 172.1] LC/MS retention time (Method A): tR=2.1 min.