Water → HCID 86652374, compound

Participants

Reaction Steps

2-((2R,4R)-4-(benzyloxy)-1-(4-bromophenyl)pyrrolidin-2-yl)acetonitrile: To a solution of 32C (0.38 g, 1.049 mmol) in dichloromethane (5.24 mL) at 0° C. was added TEA (0.292 mL, 2.098 mmol), then methanesulfonyl chloride (0.123 mL, 1.573 mmol). The reaction mixture was stirred for 1 h, and the mixture was diluted with water and dichloromethane. The layers were extracted and the organic layer was dried (MgSO4) and concentrated to give ((2S,4R)-4-(benzyloxy)-1-(4-bromophenyl)pyrrolidin-2-yl)methyl methanesulfonate (white solid, 0.53 g, 1.204 mmol, 115% yield). This white solid was then dissolved in DMSO (5 mL), and NaCN (0.206 g, 4.20 mmol) was added. The mixture was heated to 50° C. for 4 h. The reaction mixture was diluted with EtOAc, and the organic layer was washed with water, brine, dried and concentrated. Purification via silica gel chromatography gave 32D (colorless oil, 235 mg, 0.633 mmol, 60.3% yield). LC-MS Anal. Calc'd for C19H19BrN2O: 370.07. found [M+H] 372.9.

Provenance & Evidence