Dichloromethane → tert-Butyl 4-oxopiperidine-1-carboxylate

HRID 747697Notes

Reaction equation

HRID 747697 reaction equation
C(N(CC)CC)C.[C:8](=[O:19])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])OC(C)(C)C.ClCCl.[NH:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1>O>[C:15]([O:14][C:8]([N:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1)=[O:19])([CH3:16])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 337214-PiperidoneHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.7 ml (20.0 mmol) of triethylamine, 1.84 g (8.45 mmol) of di-t-butyl carbonate and 30 ml of dichloromethane were added to 1.0 g (5.0 mmol) of 4-piperidone, and the resultant mixture was stirred for 19 hours. The reaction solution was diluted with water. After the extraction with dichloromethane, the organic layer was washed with 1 N aqueous hydrochloric acid solution and then with a saturated Aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 1-t-butoxycarbonyl-4-piperidone. Separately, 80 ml of tetrahydrofuran and methyl 4-(diethoxyphosphorylmethyl)benzoate were added to 241 mg (6.0 mmol) of sodium hydride under cooling with ice, and the resultant mixture was stirred for 30 minutes and then at room temperature for 30 minutes. Crude 1-t-butoxycarbonyl-4-piperidone obtained as described above was added to the mixture, and they were stirred for 20 hours. The reaction solution was diluted with water. After the extraction with ethyl acetate, the organic layer was washed with water and then with a saturated Aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. extractionAfter the extraction with dichloromethane
  2. washthe organic layer was washed with 1 N aqueous hydrochloric acid solution
  3. dry with materialwith a saturated Aqueous NaCl solution, and then dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e55d8ccb2b0b473e8201d20050407349
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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