Reacción #7739

Ecuación de reacción

2-[2-(4-fluorophenyl)acetyl]-4-oxo-pyrazolidine-1-carboxylic acid benzyl ester

morpholine

Na(OAc)3BH

HOAc

HCl

HCl

→

desired product

Rendimiento 60.0%

2-[2-(4-fluorophenyl)acetyl]-4-morpholin-4-yl-pyrazolidine-1-carboxylic acid benzyl ester

Rendimiento 60.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothen partitioned between diethyl ether and NaHCO3
2. 2
   ExtracciónThe aqueous layer was extracted several times with ether
3. 3
   Otrodried
4. 4
   Concentraciónconcentrated in vacuo to a clear oil which
5. 5
   workup.DISSOLUTIONwas re-dissolved in ether
6. 6
   FiltraciónThe solid is collected by filtration

Procedimiento

To a solution of 2-[2-(4-fluorophenyl)acetyl]-4-oxo-pyrazolidine-1-carboxylic acid benzyl ester, 11, (0.14 g, 0.4 mmol) and morpholine (0.038 mL, 0.43 mmol) in THF at room temperature is added Na(OAc)3BH (0.125 g, 0.6 mmol) and HOAc (0.022 mL, 0.4 mmol). The solution is stirred 12 hours then partitioned between diethyl ether and NaHCO3. The aqueous layer was extracted several times with ether and the organic layers combined, dried, and concentrated in vacuo to a clear oil which was re-dissolved in ether and one equivalent of ethereal HCl is added and a white solid forms. The solid is collected by filtration and 100 mg (60% yield) of the desired product is isolated as the HCl salt.

Fuente