Tetrahydrofuran → HCID 67234333, compound

Participants

Reaction Steps

To a solution of [(3S,4R)-4-(4-chloro-phenyl)-1-(pyrrolidine-3-carbonyl)-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester (408 mg, 0.92 mmol) in THF (4 mL) was added under an atmosphere of nitrogen tetrahydro-4H-pyran-4-one (25 mg, 0.25 mmol). After stirring for 15 min. at ambient temperature sodium triacetoxyborohydride (252 mg, 1.19 mmol) was added and stirred continued for 4 h at ambient temperature. The reaction mixture was diluted with ethyl acetate (10 mL) and washed with an aqeuous solution of sodium carbonate (10 mL). The aqueous layer was extracted with ethyl acetate (10 mL) and the combined organic layers were dried of sodium sulfate. Concentration and purification by chromatography (SiO2, ethyl acetate:methanol=100:0 to 80:20) afforded the title compound (115 mg, 24%) as a light yellow oil. MS m/e: 530.3 [M]+.

Provenance & Evidence