2,2,2-Trifluoroethanol → HCID 66649805, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of [(3R,4S,5S)-5-(3,5-difluoro-4-nitro-benzyl)-4-hydroxy-tetrahydro-thiopyran-3-yl]-carbamic acid tert-butyl ester (5.0 g, 12.1 mmol, example 24f) and 2,2,2-trifluoroethanol (24.49 g, 242 mmol) was added pulverized KOH (0.694 g, 12.1 mmol) and the reaction mixture was heated at 70° C. for 3 h. The reaction mixture was evaporated and after addition of ice-water the product was extracted with EtOAc. Combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to provide the title compound after crystallization from Et2O-hexane as light yellow crystals: TLC (toluene-EtOAc 3:1) Rf=0.17; HPLC RtA=2.28 min; ESIMS [M+H-isobutylene]+=429; 1H NMR (600 MHz, DMSO-d6): δ 7.13 (s, 1H), 7.10 (d, 1H), 6.76 (d, 1H), 5.10 (s, 1H), 5.01 (m, 2H), 3.37 (m, 1H), 3.19 (dd, 1H), 2.92 (dd, 1H), 2.55 (d, 1H), 2.48 (dd, 1H), 2.37 (dd, 1H), 2.31 (d, 1H), 2.25 (dd, 1H), 1.95 (m, 1H), 1.38 (s, 9H).

Provenance & Evidence