Diisopropylethylamine → HCID 70177531, compound

Participants

Reaction Steps

Molecular sieve pellets (3 Å) were added to a solution of 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, 4-(methoxy)benzyl ester (30 mg, 0.069 mmol, Aldehyde 5), 4-(3-oxo-3-phenylpropyl)piperidine trifluoroacetate (25 mg. 0.075 mmol, from Step D), and DIEA (0.013 mL, 10 mg, 0.075 mmol) in 1,2-dichloroethane (0.70 mL). The mixture was stirred for 15 min at rt before the addition of sodium triacetoxyborohydride (17 mg, 0.080 mmol). After 2.5 h, the mixture was diluted with EtOAc (20 mL) and washed with sat'd NaHCO3 (10 mL) followed by sat'd NaCl (10 mL). The organic layer was dried (Na2SO4), decanted, and evaporated. Purification by flash column chromatography on silica gel, eluting with 15-20% EtOAc/0.5% CH3OH/CH2Cl2 gave 30 mg of the title compound as a colorless viscous oil. ESI-MS: 637 (M+H).

Provenance & Evidence