Sodium Hydroxide → HCID 58495469, compound

Participants

Reaction Steps

Under a nitrogen atmosphere add borane-dimethylsulfide complex (13.7 mL, 27.4 mmol, 2M solution in THF) to 4-[N-(tert-butoxycarbonyl)-N-(iso-propyl)-aminomethyl]-benzonitrile (1.5 g, 5.5 mmol) in THF (20 mL) at 0° C. Warm to room temperature and stir overnight. Heat the mixture under reflux for 2 h. Cool the mixture in an ice-bath and add methanol (20 mL). Warm to room temperature and add KHSO4 (7 g in 50 mL of water). Stir for 2 h at room temperature and basify with 3N aqueous NaOH. Extract with DCM, dry the organic phase over Na2SO4 and concentrate in vacuo. Purify by chromatography on silica gel (150 g) eluting with a gradient of DCM to 4:1 DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) to obtain the title compound as an oil (1.3 g, 85%). MS (APCI+) m/z: 279 (M+H)+.

Provenance & Evidence