Water → HCID 58494134, compound

HRID 1942700Notes

Reaction equation

HRID 1942700 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5]([CH2:19][CH3:20])=[C:6]([CH2:10]P(=O)(OCC)OCC)[CH:7]=[CH:8][CH:9]=1.O=[C:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1.O>O1CCCC1>[Br:3][C:4]1[C:5]([CH2:19][CH3:20])=[C:6]([CH:10]=[C:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 58494168Phosphonic acid, P-[(3-bromo-2-ethylphenyl)methyl]-, diethyl ester

Product 1

HCID 58494134HCID 58494134, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of NaH (0.155 g, 3.88 mmol) in Tetrahydrofuran (THF) (30 mL) was added diethyl [(3-bromo-2-ethylphenyl)methyl]phosphonate (D135) (1 g, 2.98 mmol) at 0° C. The reaction solution was warmed to room temperature and stirred for 1 hour. The reaction solution was cooled to 0° C. again and 1,1-dimethylethyl 4-oxo-1-piperidinecarboxylate (0.713 g, 3.58 mmol) was added. The reaction solution was warmed to room temperature and stirred overnight. Water was added and extracted with ethyl acetate, the organic phases were dried over sodium sulphate, concentrated and purified by ISCO column chromatography to afford 1,1-dimethylethyl 4-[(3-bromo-2-ethylphenyl)methylidene]-1-piperidinecarboxylate (D136) (0.73 g). MS (ES): C19H26BrNO2 requires 379.1. found 324.1 (M+H+-56).

Workup

  1. temperatureThe reaction solution was cooled to 0° C. again
  2. temperatureThe reaction solution was warmed to room temperature
  3. stirringstirred overnight
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic phases were dried over sodium sulphate
  6. concentrationconcentrated
  7. custompurified by ISCO column chromatography

Sources & evidence

ORD record
ord-257825dd7c8c4211b7b8a748741294d1
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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