HCID 86656432, compound → HCID 67352034, compound

Participants

Reaction Steps

(1R,6S)-2,2-difluoro-6-hydroxy-N-[(1R)-1-phenylethyl]cyclohexanaminium trifluoroacetate (74) in a solution of methanol (1.5 mL) was exposed to Pd/C (409 mg, 0.384 mmol) and hydrogen atmosphere (1 atm). The heterogeneous reaction mixture was filtered through a plug of celite and washed three times with 30 mL of methanol. The filtrate was concentrated under reduced pressure to yield (1R,6S)-2,2-difluoro-6-hydroxycyclohexanaminium trifluoroacetate (75) in quantitative yield. 1H NMR (500 MHz, CD3OD) δ 3.68 (s, 1H), 3.34 (t, J=16.6, 2H), 2.19 (s, 1H), 2.06 (s, 1H), 1.87 (d, J=56.3, 2H), 1.49 (s, 2H), 19F NMR (470 MHz, cd3od) δ −77.30 (s, 3F), −99.95 (d, J=242.9, 1F), −114.48-−116.71 (m, 1F).

Provenance & Evidence