Water → HCID 59396006, compound

Participants

Reaction Conditions

Reaction Steps

To an ice cooled solution of phenylmethyl (1S,4S,6S)-4-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate D8 (0.930 g) in pyridine (14 ml) was added HF-pyridine (2.642 ml, 30.4 mmol), the resulting mixture was stirred for 20 minutes at 0° C. and then was slowly warmed to room temperature and stirred for 30 minutes. Water (200 ml) and EtOAc (30 ml) were added and stirred for 15 minutes. The organic phase was separated and the aqueous phase was extracted with EtOAc (6×5 mls). The collected organic layers were dried (Na2SO4), filtered and evaporated under reduced pressure to obtain an oil which was purified via Companion CombiFlash (Silica gel, SNAP 100 g column; eluted with 20 CV of DCM/MeOH 98/2). Collected and evaporated fractions gave the title compound D9 (0.447 g). MS: (ES/+) m/z: 262 (M+1). C15H19NO3 requires 261. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.51-7.24 (m, 5 H), 5.20-5.0 (m, 2 H), 4.73-4.48 (m, 1 H), 4.43-4.17 (m, 1 H), 3.71-3.51 (m, 1 H), 3.51-2.35 (m, 2 H), 2.46-2.24 (m, 2 H), 1.20-0.95 (m, 2 H), 0.95-0.59 (m, 2 H), 0.21-0.09 (m, 1 H).

Provenance & Evidence