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

HRID 980605Notes

Reaction equation

HRID 980605 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 AcetateSolvent2×

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 ethyl acetate 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-f59aa353d8574e30b9daeb1ff8ee20bd
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

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