p-Toluenesulfonic acid → HCID 57421405, compound

Participants

Reaction Conditions

Reaction Steps

Into a 250 mL 3-necked round bottom flask was placed a solution of benzyl 3-hydroxypyrrolidine-1-carboxylate (10 g, 45.23 mmol) in CH2Cl2 (100 mL). To this was added 3,4-dihydro-2H-pyran (19 g, 226.19 mmol). To the mixture was added p-toluenesulfonic acid (389 mg, 2.26 mmol) and the resulting solution was allowed to react, with stirring, for 10 minutes while the temperature was maintained at 0° C. The resulting solution was allowed to react, with stirring, for an additional 1 hour at room temperature. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:2). The reaction mixture was then quenched by the adding 100 mL of NaHCO3. The resulting mixture was washed with 100 mL of NaHCO3 and 100 mL of brine. The mixture was dried over MgSO4 and concentrated under vacuum using a rotary evaporator. This resulted in 15 g (98%) of benzyl 3-(tetrahydro-2H-pyran-2-yloxy)pyrrolidine-1-carboxylate as yellow oil.

Provenance & Evidence