Dimethylformamide → Ethyl 5-(1-benzyloxycarbonyl-4-piperidyl)valerate

HRID 980608Notes

Reaction equation

HRID 980608 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].[CH2:29](I)[CH3:30].CN(C)C=O>O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:29][CH3:30])=[O:22])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340Iodoethane2×HCID 516892Sodium BicarbonateHCID 201437225-(1-Benzyloxycarbonyl-4-piperidyl)valeric acid

Product 1

HCID 14046929Ethyl 5-(1-benzyloxycarbonyl-4-piperidyl)valerate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 54.8 g of 5-(1-benzyloxycarbonyl-4-piperidyl)valeric acid, 29 g of sodium hydrogencarbonate, 21 ml of ethyl iodide and 150 ml of N,N-dimethylformamide is heated at 70° to 80° C. with stirring for 3 hours. Ethyl iodide (10 ml) is additionally added to the reaction solution, followed by heating at 90° to 100° C. for 3 hours. After cooling, 1 l of water is added to the reaction solution, and the mixture is extracted with 1 l of ethyl acetate. The extract is washed with water, 1N hydrochloric acid and dilute aqueous sodium hydrogencarbonate solution successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 58 g of ethyl 5-(1-benzyloxycarbonyl-4-piperidyl)valerate as pale yellow oil.

Workup

  1. temperatureis heated at 70° to 80° C.
  2. temperatureby heating at 90° to 100° C. for 3 hours
  3. temperatureAfter cooling
  4. extractionthe mixture is extracted with 1 l of ethyl acetate
  5. washThe extract is washed with water, 1N hydrochloric acid and dilute aqueous sodium hydrogencarbonate solution successively
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e7768f4326cd4550a4ce39bc5095392c
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

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