Sodium Hydroxide → HCID 69039795, compound

Participants

Reaction Steps

A solution of [(1R,2S)-2-formyl-2-(3-oxo-propyl)-cyclohexyl]-carbamic acid tert-butyl ester (4.73 g, 16.7 mmol) and 4-fluorobenzylamine (2.3 g, 18 mmol) in dichloromethane (50 mL) was cooled in an ice bath and treated with sodium triacetoxyborohydride (10.1 g, 48 mmol). The resulting mixture was then stirred at room temperature overnight. The mixture was treated with 1.0 N aqueous sodium hydroxide (25 mL) and stirred at room temperature for 1 hour. The organic phase was removed and washed with water and saturated aqueous sodium chloride. The solvent was removed under vacuum to give a residue. The residue was purified by chromatography on silica gel, eluting with 60% ethyl acetate/hexane, to give an oil (6.3 g). 1H NMR (300 MHz, CDCl3) δ7.31-7.24 (m, 2H), 6.97-6.94 (m, 2H), 4.82 (bm, 1H), 3.62 (m, 1H), 3.37 (bs, 2H), 2.42 (m, 1H), 2.20 (m, 3H), 1.69-1.21 (m, 12H), 1.45 (s, 9H). Mass spec (ES+) m+/z 377.2 (M+H+).

Provenance & Evidence