Reaction #312615

Reaction equation

4-nitrophenyl chloroformate

pyridine

4-(4-amino-2-chlorophenyl)morpholin-3-one

tert-butyl pyrazolidine-1-carboxylate

N-ethyldiisopropylamine

→

tert-Butyl 2-[3-chloro-4-(3-oxomorpholin-4-yl)phenylcarbamoyl]pyrazolidine-1-carboxylate

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGAfter stirring at RT for 20 h
2. 2
   Othergiving 420 mg (57.3%) of step 1

Procedure

340 mg (1.5 mmol) of 4-(4-amino-2-chlorophenyl)morpholin-3-one are dissolved in 10 ml of dichloromethane (DCM), 302 mg (1.5 mmol) of 4-nitrophenyl chloroformate and 121 μl (1.5 mmol) of pyridine are subsequently added successively, and the mixture is stirred at RT for 1 h. 300.0 mg (0.7 mmol) of tert-butyl pyrazolidine-1-carboxylate and 0.765 mg (4.5 mmol) of N-ethyldiisopropylamine are added to this reaction mixture. After stirring at RT for 20 h, the mixture is subjected to conventional work-up, giving 420 mg (57.3%) of step 1; MS (FAB) m/e=425/427 (M+H)+.

Source