p-Toluenesulfonic acid → HCID 66861533, compound

Participants

Reaction Steps

tert-butyl (2S,3R)-3-hydroxy-4-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-1-(tetrahydro-2H-pyran-4-yl)butan-2-ylcarbamate (180 mg, 0.4 mmol) was dissolved in a minimal volume of Et2O (5 mL) and added to a solution of TsOH (76 mg, 0.44 mmol) in EtOH (15 mL). The solution was placed on a rotary evaporator and the Et2O was removed at rt. The flask was then lowered into the water bath and the selective deprotection of the Boc group proceeded concurrent with removal of the remainder of solvent. The reaction was completed after 2 h and gave a white solid. The residue was dissolved in EtOH/H2O (1:1, 50 mL) and washed with hexane/EtOAc (5:1, 3×15 mL). 1N aq NaOH was added until the pH>10 and the mixture was extracted with EtOAc (3×15 mL). The organic layers were combined, washed with brine, dried over Na2SO4, filtered and concentrated to give 2-(trimethylsilyl)ethyl (2R,3S)-3-amino-2-hydroxy-4-(tetrahydro-2H-pyran-4-yl)butyl(methyl)carbamate (100 mg, 72%).

Provenance & Evidence