Acetic Acid → HCID 22562204, compound

Participants

Reaction Steps

To a stirred solution of 1-[1-(1-phenylcycloheptyl)-4-piperidinyl]-1H-benzimidazole-2-carbaldehyde (this was prepared in preparation 10, 159 mg, 0.396 mmol) and t-butyl (1S,4S)-(−)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (86 mg, 0.436 mmol) in 1,2-dichloroethane (4 ml) was added NaBH(OAc)3 (117 mg, 0.554 mmol) and acetic acid (48 μl, 0.832 mmol) at room temperature. After 24 hour stirring, the reaction mixture was quenched with NaHCO3 solution and extracted with CH2Cl2. The extracts combined were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC (1 mm thick plate×2, acetone/n-hexane:1/3) to afford 227 mg (98%) of title compound as colorless foam.

Provenance & Evidence