Reaktion #7761

Reaktionsgleichung

Morpholine-4-carboxylic acid 1-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester

2-phenoxypyrimidine-4-carbonyl chloride

NaOH

→

desired product

Ausbeute 61.0%

morpholine-4-carboxylic acid 1-[2-(4-fluorophenyl)acetyl]-2-(2-phenoxypyrimidine-4-carbonyl)-pyrazolidin-4-yl ester

Ausbeute 61.0%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 3 hours
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITcontinued for an additional 12 hours
5. 5
   Waschenwashed with water (50 mL)
6. 6
   WaschenThe combined organic layers are washed with NaHCO3 (sat.) (50 mL) and brine (50 mL)
7. 7
   Sonstigedried
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    Sonstigeto provide a brown oil
11. 11
    SonstigeThe crude material is purified over silica (100% ethyl acetate to 5% methyl alcohol/ethyl acetate)

Vorschrift

Morpholine-4-carboxylic acid 1-[2-(4-fluorophenyl)acetyl]-pyrazolidin-4-yl ester, 41, (354 mg, 1.05 mmol) and 2-phenoxypyrimidine-4-carbonyl chloride, 18, (345 mg, 1.47 mmol) are dissolved in dichloromethane (2 mL). 1.0 N NaOH (3 mL) is added dropwise at room temperature while vigorously stirring. The reaction is allowed to proceed for 12 hours after which time additional acid chloride, 18, is added and stirring continued for 3 hours. Additional acid chloride, 18, (83 mg) is added and stirring continued for an additional 12 hours. After which time the reaction is diluted with dichloromethane (50 mL) and washed with water (50 mL). The combined organic layers are washed with NaHCO3 (sat.) (50 mL) and brine (50 mL), dried, filtered and concentrated to provide a brown oil. The crude material is purified over silica (100% ethyl acetate to 5% methyl alcohol/ethyl acetate) afford 348 mg (61% yield) of the desired product as a viscous oil.

Quelle