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

HRID 983813Notes

Reaction equation

HRID 983813 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% h).

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
  8. customafforded a white solid (33.6 g, yield 38.2% h)

Sources & evidence

ORD record
ord-499fd895e0dd45fabd8eadf095603548
Source dataset
uspto-grants-2005_03
Patent number
US06867202B1

Reaction notes

Loading…