Reaction #1379917

Reaction equation

benzyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Intermediate 1

benzyl (3R)-3-hydroxypyrrolidine-1-carboxylate

N-methylmorpholine-N-oxide

→

title compound

Benzyl 3-oxopyrrolidine-1-carboxylate

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherbelow 30° C.
2. 2
   workup.ADDITIONThe mixture was poured onto a plug of 5 kg of silica gel
3. 3
   Washeluted with 10% ethyl acetate/dichloromethane

Procedure

A 12-L, 3 neck round bottom flask equipped with a mechanical stirrer, thermocouple, condenser, and nitrogen bubbler was charged with 351 g (1.61 mol) of benzyl (3R)-3-hydroxypyrrolidine-1-carboxylate (Intermediate 1, Step A), 6 L of dichloromethane, 500 g of powdered molecular sieves, and 400 g (3.41 mol) of N-methylmorpholine-N-oxide. The resultant suspension was stirred at ambient temperature and to this was added 12.9 g (0.0367 mol) of tetrapropylammonium perruthenate. The reaction temperature was kept at or below 30° C. with a cold water bath. The mixture was stirred at ambient temperature for 2 h. The mixture was poured onto a plug of 5 kg of silica gel and eluted with 10% ethyl acetate/dichloromethane to give the title compound as an orange oil.

Source