Sodium Hydroxide → HCID 58495631, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, add borane-dimethylsulfide complex (29.3 mL, 58.7 mmol, 2M solution in THF) to 4-[N-(tert-butoxycarbonyl)-N-(cyclohexyl)-aminomethyl]-benzonitrile (3.7 g, 11.7 mmol) in THF (100 mL) at 0° C. Warm to room temperature and stir overnight. Heat the mixture under reflux for 30 min. Cool the mixture in an ice-bath, and add methanol (20 mL). Warm to room temperature, and add KHSO4 (20 g in 100 mL of water). Stir the mixture for 2 h and adjust the pH to 10 with 3N aqueous NaOH. Extract the mixture with DCM. Dry the organic phase over Na2SO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel (150 g) eluting with a gradient of DCM to 1:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain the title compound as an oil (2.43 g, 65%). MS (ES+) m/z: 319 (M+H)+.

Provenance & Evidence