Hydrogen Peroxide → HCID 56608405, compound

Participants

Reaction Steps

A solution of 1-benzyloxycarbonyl-4-phenyl-1,2,3,6-tetrahydropyridine (1.0 g) in tetrahydrofuran (20 mL) was cooled to 0° C. and treated with borane:tetrahydrofuran (3.75 mL of 1M solution in tetrahydrofuran). The reaction mixture was stirred for 16 hours at ambient temperature, diluted with methanol (50 mL), and treated with 3N sodium hydroxide (1.25 mL). The resulting reaction mixture was cooled to 0° C. and treated with 30% hydrogen peroxide solution (0.58 mL). After refluxing for 2 hours, the reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined organic layers were washed with water and the aqueous layer was extracted with ethyl acetate. Combined organic layers were dried and evaporated to afford the crude product (0.88 g). Chromatography, eluting with hexane:ethyl acetate (3:1) afforded the trans-1-benzyloxycarbonyl-3-hydroxy-4-phenylpiperidine (0.31 g); MS: m/z=312(M+1); NMR: 1.54-1.72 (m, 2), 3.51 (m, 1), 4.02 (m, 1), 4.17 (m, 1), 4.86 (d, 1, J=5), 5.1 (s, 2), 7.17-7.37 (m, 10).

Provenance & Evidence