Trifluoromethanesulfonic anhydride → HCID 53725706, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 500 mg (2.32 mmol) of 1-t-butoxycarbonyl-4-(hydroxymethyl)piperidine (Example 201) and 1 mL (4.5 mmol) of 2,6-di-t-butylpyridine in 10 mL of CH2Cl2 was added 0.4 mL (2.32 mmol) of triflouromethanesulfonic anhydride at −78° C. After stirring for 0.5 h, 0.5 mL (4.5 mmol) of benzylmercaptane were added. The mixture was warmed to 0° C. and allowed to stir for another 15 min. 10 mL of sat'd NaHCO3 solution were added and the mixture was extracted with CH2Cl2. The combined organic fractions were washed with sat'd NaHCO3 solution and sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 4:1) to give the title compound.

Provenance & Evidence