Acetic Acid → HCID 86616092, compound

Participants

Reaction Steps

To a solution of (S)-9-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-2,2-difluoro-6,7,8,9-tetrahydro-1,3-dioxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester (0.26 mmol) in DCM (5 mL) add trifluoroacetic acid (1 mL). After stirring for 1 h, quench the reaction with sodium bicarbonate (5 mL) and dilute with DCM (20 mL). Separate and dry the organics over sodium sulfate. Remove the solvent and chromatograph the product using ethyl acetate/hexane (5-20%) to elute. This provides N-(3,5-Bis-trifluoromethyl-benzyl)-N-(2,2-difluoro-6,7,8,9-tetrahydro-5H-1,3-dioxa-5-aza-cyclohepta[f]inden-9-yl)-acetamide as an oil. To this crude intermediate in DCE (dichloroethane) (5 mL), add cyclopentylcarbaldehyde (1.3 mmol), acetic acid (cat.), and sodium triacetoxyborohydride (1.6 mmol). After stirring for 14 h, dilute the reaction with DCM (20 mL) and quench with concentrated sodium carbonate (5 mL). Separate the organics, dry over sodium sulfate, and remove solvent under vacuum. Chromatograph the product using ethyl acetate/hexane (5-20%) to elute. This provides the title compound as a foam. MS (ES+): 593 (M+H).

Provenance & Evidence