Sodium borohydride → HCID 66953995, compound

Participants

Reaction Steps

To a solution of N-(3,5-dimethoxybenzyl)-4-oxoadamantane-1-carboxamide (230 mg, 0.670 mol) in anhydrous CH3OH was added NaBH4 (100 mg, 2.7 mmol) at 0° C. The reaction mixture was stirred for 1 h at rt. The solvent was removed under reduced pressure, diluted with CH2Cl2 and washed with water. The organic layer was separated, dried, and concentrated to give N-(3,5-dimethoxybenzyl)-4-hydroxyadamantane-1-carboxamide (230 mg, 100%). 1H NMR: (400 MHz, CDCl3): δ=1.40 (d, 1H), 1.46-1.62 (m, 6H), 1.70-1.82 (m, 5H), 1.84-1.95 (m, 3H) 2.01-2.14 (m, 2H), 3.75 (s, 3H), 3.80 (s, 3H), 3.82 (s, 1H), 4.29 (d, 2H), 5.98 (s, 1H), 6.40 (m, 0.2H), 7.08 (d, 1H).

Provenance & Evidence