Benzaldehyde → N-[2-({(3R)-1-[cis-2-(Benzylamino)cyclohexyl]pyrrolidin-3-yl]amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide

Participants

Reaction Steps

To a mixture of benzaldehyde (0.061 mL, 0.6 mmol) and N-(2-{[(3R)-1-(cis-2-aminocyclohexyl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide (0.278 g, 0.60 mmol) in CH2Cl2 (10 mL) was added NaB(OAc)3H (0.128 g, 0.60 mmol). After being stirred overnight at room temperature under N2, the reaction mixture was diluted with EtOAc and washed with saturated Na2CO3. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), concentrated and flash chromatographed (EtOAc to EtOAc:MeOH:Et3N=9:1:0.5) to give 0.21 g of the title compound. MS (EI) calcd: (M+H)+=503.3. Found: 503.4.

Provenance & Evidence