Dichloromethane → HCID 45100810, compound

Participants

Reaction Conditions

Reaction Steps

Sodium borohydride (11 mg, 0.28 mmol) was added at RT to a solution of 4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-2-[3-methyl-2-oxo-4-(3-trifluoromethoxy-phenyl)-piperazin-1-yl]-butyric acid methyl ester (70 mg, 0.14 mmol) in EtOH (2 mL), then after 16 min another portion of sodium borohydride (11 mg, 0.28 mmol) was added. After 24 h another portion of sodium borohydride (30 mg, 0.80 mmol) was added and the reaction mixture heated at 60° C. for 6 h. After cooling 10% aq. KHSO4 solution and CH2Cl2 were added to the reaction mixture, the organic layer washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; CH2Cl2/MeOH 4:1, then CH2Cl2/MeOH/25% aq. ammonia solution 80:20:1) afforded 4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-2-[3-methyl-2-oxo-4-(3-trifluoromethoxy-phenyl)-piperazin-1-yl]-butyric acid (41 mg, 60%; light yellow solid, MS: 484.2 (M−H)−) and 1-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-1-hydroxymethyl-propyl]-3-methyl-4-(3-trifluoromethoxy-phenyl)-piperazin-2-one (22 mg, 33%; colorless oil, MS: 472.2 (M+H)+).

Provenance & Evidence