Sodium borohydride → HCID 58046697, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 3-((4-oxo-8-(4-oxo-4-phenylbutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (1.45 g, 2.56 mmol, 1 equiv) in ethanol was warmed to 41° C. Sodium borohydride (194 mg, 5.13 mmol, 2 equiv) was slowly added and the reaction stirred as such for 30 minutes. It was stirred at room temperature for 16 h. The reaction was concentrated in vacuo and the mixture was partitioned between ethyl acetate and water, followed by a brine wash. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified using the Biotage flash chromatography system (SNAP 50 g cartridge, Rf=0.45, gradient—1%-10% methanol in dichloromethane) to afford the title compound as a cream solid (1.2 g, 83%); 1H NMR (400 MHz, DMSO-d6): δ 1.52 (s, 9H); 1.59-1.66 (m. 5H); 2.33-2.34 (m, 2H); 2.51-2.52 (m, 2H); 2.68-2.73 (m, 4H); 4.57-4.61 (m, 5H); 5.51 (d, 1H, J=3.6 Hz); 6.74-6.77 (m, 1H); 6.82 (s, 2H); 6.85 (s, 1H); 7.18-7.23 (m, 3H); 7.29-7.36 (m, 4H); 7.5-7.53 (m, 2H); 7.79 (bs, 1H); 7.82-7.84 (m, 1H); MS for C35H43N3O4 m/z 570.33 (M+H)+.

Provenance & Evidence