Pyridine → HCID 59003227, compound

Participants

Reaction Steps

To a solution of (S)-9-Amino-2,2-difluoro-6,7,8,9-tetrahydro-1,3-dioxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester (1.8 mmol) in DCE (20 mL), add 3,5-bis(trifluoromethyl)benzylaldehyde (2.8 mmol), acetic acid (cat.), and Sodium triacetoxyborohydride (5.7 mmol). After stirring for 14 h, dilute with DCM (100 mL) and quench with concentrated sodium carbonate (50 mL). Separate the organics, dry over sodium sulfate, and remove solvent under vacuum. Chromatograph using ethyl acetate/hexane (5-25%) to elute. This provides (S)-9-(3,5-Bis-trifluoromethyl-benzylamino)-2,2-difluoro-6,7,8,9-tetrahydro-1,3-dioxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester as an oil. MS (ES+): 569 (M+H). To a solution of (S)-9-(3,5-Bis-trifluoromethyl-benzylamino)-2,2-difluoro-6,7,8,9-tetrahydro-1,3-dioxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester (0.35 mmol) in DCM (5 mL), add pyridine (1.06 mmol) and acetyl chloride (1.06 mmol). After stirring for 1.5 h remove solvent under vacuum and chromatograph using ethyl acetate/hexane (5-25%) to elute. This provides the title compound as a foam. MS (ES+): 609 (M−H).

Provenance & Evidence