Benzyl Bromide → 1-[(1,1-Dimethylethoxycarbonyl)amino]-piperidine-4-carboxylic acid benzyl ester

HRID 556301Notes

Reaction equation

HRID 556301 reaction equation
[CH3:1][C:2]([CH3:17])([O:4][C:5]([NH:7][N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:6])[CH3:3].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CO.O>[CH2:24]([O:15][C:14]([CH:11]1[CH2:12][CH2:13][N:8]([NH:7][C:5]([O:4][C:2]([CH3:17])([CH3:1])[CH3:3])=[O:6])[CH2:9][CH2:10]1)=[O:16])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 667420541-[(1,1-Dimethylethoxycarbonyl)amino]-piperidine-4-carboxylic acid

Product 1

HCID 667416331-[(1,1-Dimethylethoxycarbonyl)amino]-piperidine-4-carboxylic acid benzyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-[(1,1-Dimethylethoxycarbonyl)amino]-piperidine-4-carboxylic acid (6 g, 26.16 mmol, 1 eq.), from step 1, was dissolved in methanol (150 ml) and cesium carbonate (4.26 g, 13.08 mmol, 0.5 eq.) was added. The mixture was stirred at room temperature for 2 h, the solvent was removed under reduced pressure. The crude was dissolved in DMF (100 ml) and benzylbromide (5.37 g, 31.39 mmol, 1.2 eq.) was added dropwise. The mixture was stirred overnight at room temperature and poured in water (300 ml), extracted with Ethyl Acetate (900 ml) The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to give a white solid. Yield 95%, 7 g.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe crude was dissolved in DMF (100 ml)
  3. stirringThe mixture was stirred overnight at room temperature
  4. extractionextracted with Ethyl Acetate (900 ml) The organic layer
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. customto give a white solid

Sources & evidence

ORD record
ord-f667bb2bd4c64234a19649415b86ed60
Source dataset
uspto-grants-2011_11
Patent number
US08058262B2

Reaction notes

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