Sodium borohydride → HCID 66673152, compound

Participants

Reaction Steps

Add NaBH4 (79.4 mg, 2.10 mmol) to a suspension of 6-(5-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-nicotinamide (Intermediate 2, 395 mg, 1.40 mmol) in MeOH (10 ml), stirring at ambient temperature. After 24 hours, concentrate the reaction mixture and redissolve in EtOAc. Wash with 5% aqueous KOH, water, and brine before drying (MgSO4) and concentrating to a solid. Purify material on silica gel (50% THF/DCM) to give 6-(5-Hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-nicotinamide (288 mg) as a white solid. Mass spectrum (ion spray): m/z=285 (M+1); 1HNMR (CDCl3): 8.58 (s, 1H), 8.16 (d, 1H), 7.50 (d, 1H), 6.97 (m, 2H), 6.88 (s, 1H), 5.95 (broad, 2H), 4.80 (t, 1H0, 2.82-2.74 (m, 2H), 2.03-1.77 (m, 4H), 1.68 (s, 1H).

Provenance & Evidence