Sodium triacetoxyborohydride → HCID 57236775, compound

Participants

Reaction Steps

Molecular sieve pellets (3 A) were added to a solution of 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid (4-methoxy)benzyl ester (34 mg, 0.078 mmol, from EXAMPLE 33, Step E) and 4-(3,3-difluoro-3-phenylpropyl)piperidine (20 mg. 0.084 mmol, from EXAMPLE 154, Step D) in 1,2-dichloroethane (0.75 mL). The mixture was stirred for 45 min. at RT before the addition of sodium triacetoxyborohydride (19.9 mg, 0.094 mmol). After 4 h, the mixture was diluted with EtOAc (20 mL) and washed with saturated aq. NaHCO3 (10 mL) followed by saturated aq. NaCl (10 mL). The organic layer was dried (Na2SO4), decanted, and evaporated. Purification by flash column chromatography on silica gel, eluting with 92:8 v/v, then 86:14 v/v hexanes/EtOAc, gave 34 mg of the title compound as a colorless film. 1H NMR (400 MHz, CD3OD) δ 7.47-7.40 (m, 5H), 7.36 (d, J=8,22H), 7.23 (t, J=7, 2H), 7.15 (t, J=7, 1H), 7.10 (d, J=7, 1H), 6.90 (d, J=8, 2H), 5.12 (s, 2H), 3.18 (dd, J=9, 7, 1H), 3.12-3.06 (m, 2H), 2.80-2.56 (m, 4H), 2.51 (dd, J=9, 7, 11H), 2.30-2.19 (m, 3H), 2.12 (tm, J=16, 2H), 1.94 (bd, J=12, 1H), 1.86-1.50 (m, 9H), 1.31-0.89 (m, 10H); ESI-MS 659 (M+H).

Provenance & Evidence