Sodium Hydroxide → HCID 58495673, compound

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Reaction Steps

Under a nitrogen atmosphere, add borane-dimethylsulfide complex (13 mL, 26 mmol, 2M solution in THF) to 4-[N-(tert-butoxycarbonyl)-N-(iso-butyl)-aminomethyl]-benzonitrile (1.5 g, 5.2 mmol) in THF (20 mL) at 0° C. Heat the mixture under reflux overnight. 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 (0.72 g, 47%). MS (APCI+) m/z: 293 (M+H)+.

Provenance & Evidence