Reaction #1178451

Reaction equation

ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate

N-Boc-D-proline

4-chloroaniline

→

tert-butyl (R)-2-(4-chlorophenyl-carbamoyl)pyrrolidine-1-carboxylate

Solvents

toluene

Conditions

Workup

1. 1
   FiltrationThe reaction mixture is filtered
2. 2
   workup.ADDITIONpetroleum ether is added to the filtrate
3. 3
   OtherThe precipitate formed
4. 4
   Filtrationis filtered off
5. 5
   Otherdried

Procedure

4.82 g (19.5 mmol) of ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate (EEDQ) are added to a suspension of 2.80 g (13.0 mmol) of N-Boc-D-proline and 1.66 g (13.0 mmol) of 4-chloroaniline in 50 ml of toluene, and the mixture is stirred at room temperature for 3 hours. The reaction mixture is filtered, and petroleum ether is added to the filtrate. The precipitate formed is filtered off and dried, giving tert-butyl (R)-2-(4-chlorophenyl-carbamoyl)pyrrolidine-1-carboxylate as colourless crystals; ESI 325.

Source