Reaktion #7739

Reaktionsgleichung

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

morpholine

Na(OAc)3BH

HOAc

HCl

HCl

→

desired product

Ausbeute 60.0%

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

Ausbeute 60.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethen partitioned between diethyl ether and NaHCO3
2. 2
   ExtraktionThe aqueous layer was extracted several times with ether
3. 3
   Sonstigedried
4. 4
   Einengenconcentrated in vacuo to a clear oil which
5. 5
   workup.DISSOLUTIONwas re-dissolved in ether
6. 6
   FiltrationThe solid is collected by filtration

Vorschrift

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.

Quelle