Sodium Bicarbonate → 4,4-Difluorocyclohexanecarboxylic acid

Participants

Reaction Steps

To 19 mg (0.08 mmol) of 1,3-diethyl-bicyclo[3.2.1]-1β,3,8-triaza-spiro[4.5]dodecan-2-one and 23.6 mg (0.08 mmol) of 4,4-difluoro-cyclohexanecarboxylic acid ((S)-3-oxo-1-phenyl-propyl)-amide was added 1.5 mL of anhydrous DCE and 26.7 mg (0.12 mmol) of sodium triacetoxyborohydride. After an overnight agitation, 2 mL of saturated solution of sodium bicarbonate was added. The solution was then extracted with DCM (2×2 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The crude mixture was purified by semi-preparative HPLC (Method A) to yield 17.7 mg (40%) of 4,4-difluoro-cyclohexanecarboxylic acid {(S)-3-[1,3-diethyl-bicyclo[3.2.1]-2-oxo-1β,3,8-triaza-spiro[4.5]dodec-8-yl]-1-phenyl-propyl}-amide hydrochloride.

Provenance & Evidence