Dimethylformamide → 1-Tert-butyl 3-ethyl 3-benzyl-4-oxopiperidine-1,3-dicarboxylate

HRID 986986Notes

Reaction equation

HRID 986986 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7]1)=[O:5])[CH3:2].CN(C=O)C.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH2:1]([O:3][C:4]([C:6]1([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 64208761-(1,1-Dimethylethyl) 3-ethyl 4-oxo-1,3-piperidinedicarboxylate

Product 1

HCID 541303761-Tert-butyl 3-ethyl 3-benzyl-4-oxopiperidine-1,3-dicarboxylateYield 38.2%

Conditions

Temperature
60 °C

Procedure

To a solution of 4-oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (73.36 g, 0.27 mol) in DMF (734 mL) lithium carbonate (50 g, 0.676 mol) was added, followed by benzyl bromide (55.44 g, 0.324 mol). The mixture was heated to about 60° C. and stirred for about 20 hours. The reaction mixture was then cooled to room temperature and extracted with IPE, washed with water and dried over magnesium sulfate. After filtration and concentration in vacuo a solid was obtained. Recrystallization of the crude product in hexane afforded a white solid (33.6 g, yield 38.2%).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionextracted with IPE
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration and concentration in vacuo a solid
  6. customwas obtained
  7. customRecrystallization of the crude product in hexane

Sources & evidence

ORD record
ord-97b1218ea0b94f1eb8a83ed83c9bc0a6
Source dataset
uspto-grants-2003_10
Patent number
US06630487B2

Reaction notes

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