Dimethylformamide → 3-[3-(1-Benzyloxycarbonyl-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1269486Notes

Reaction equation

HRID 1269486 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH2:25][CH:24]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]([C:38]([OH:40])=[O:39])([CH3:37])[CH3:36])[CH:29]=2)[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].CN(C)C=O>O>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH2:25][CH:24]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([O:34][C:35]([C:38]([O:40][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:39])([CH3:37])[CH3:36])[CH:29]=2)[CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 688861023-[3-(1-Carboxy-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 688845133-[3-(1-Benzyloxycarbonyl-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Cesium carbonate (24.00 g, 73.67 mmol) and benzyl bromide (8.03 mL, 67.53 mmol) were added sequentially to a solution of of 3-[3-(1-Carboxy-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester (22.31 g, 61.39 mmol) and dimethylformamide (100 mL) at ambient temperature. The resulting mixture was warmed to 60° C., stirred 1.5 h, cooled to ambient temperature and diluted with water (600 mL). The aqueous solution was extracted with diethyl ether (2×300 mL). The organic extracts were combined and washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resultant oil was purified by flash column chromatography (7:1 hexanes/ethyl acetate) to provide 3-[3-(1-Benzyloxycarbonyl-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid tert-butyl ester as a pale-yellow oil.

Workup

  1. temperaturecooled to ambient temperature
  2. extractionThe aqueous solution was extracted with diethyl ether (2×300 mL)
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant oil was purified by flash column chromatography (7:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e6ee4622fa4f41a5bfb0754789a37303
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

Loading…