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

HRID 280977Notes

Reaction equation

HRID 280977 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 5-(1-benzyloxycarbonyl-4-piperidyl)valeric acid (54.8 g), sodium bicarbonate (29 g), ethyl iodide (21 ml) and N,N-dimethylformamide (150 ml) is stirred for 3 hours at 70°-80° C. After further addition of ethyl iodide (10 ml), the stirring is continued for further 3 hours at 90°-100° C. After cooling, the mixture is diluted with water and extracted with ethyl acetate (1 l). The extract is washed successively with water, 1N hydrochloric acid and sodium bicarbonate solution, dried over anhydrous magnesium sulfate and evaporated in vacuo to yield ethyl 5-(1-benzyloxycarbonyl-4-piperidyl)valerate (58 g) as a pale yellow oil.

Workup

  1. waitthe stirring is continued for further 3 hours at 90°-100° C
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate (1 l)
  4. washThe extract is washed successively with water, 1N hydrochloric acid and sodium bicarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-64bdf880f2f44400ab9b2d2427ec7b46
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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