Water → Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate

HRID 649395Notes

Reaction equation

HRID 649395 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH:19](O)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:28])=O.O>C(OCC)(=O)C.N1C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH:19]([Cl:28])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 20143718Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate

Product 1

HCID 20143712Ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a mixture of 200 ml of ethyl acetate and 12 g of pyridine is dissolved 11.5 g of ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-hydroxybutyrate, and 5 ml of thionyl chloride is added to the solution, followed by refluxing with stirring for 1 hour. After cooling, 500 ml of water and 100 ml are added to the reaction solution, followed by extraction. The extract is washed with 0.1N hydrochloric acid and water successively, dried over anhydrous magnesium sulfate and treated with activated carbon. The ethyl acetate is evaporated off to give 10.5 g of ethyl 4-(1-benzyloxycarbonyl-4-piperidyl)-2-chlorobutyrate pale yellow oil.

Workup

  1. additionis added to the solution
  2. temperatureby refluxing
  3. temperatureAfter cooling
  4. extractionfollowed by extraction
  5. washThe extract is washed with 0.1N hydrochloric acid and water successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. additiontreated with activated carbon
  8. customThe ethyl acetate is evaporated off

Sources & evidence

ORD record
ord-b1c953223215493fa8c27391a107f1f3
Source dataset
uspto-grants-1988_04
Patent number
US04739066

Reaction notes

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