Water → Benzyl 1-Boc-piperidine-3-carboxylate

HRID 602125Notes

Reaction equation

HRID 602125 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:15]([O:19][C:20]([N:22]1[CH2:30][CH2:29][CH2:28][CH:24]([C:25]([OH:27])=[O:26])[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].O>CN(C)C=O>[C:15]([O:19][C:20]([N:22]1[CH2:30][CH2:29][CH2:28][CH:24]([C:25]([O:27][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:26])[CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acid

Product 1

HCID 20723878Benzyl 1-Boc-piperidine-3-carboxylateYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (4.34 g, 25.4 mmol) and potassium carbonate (4.80 g, 34.7 mmol) were added to 1-(tert-butoxycarbonyl)nipecotic acid (5.30 g, 23.1 mmol) in N,N-dimethylformamide (20 mL). The mixture was stirred at room temperature for 6 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate. The organic layer washed sequentially with water and brine and was dried over sodium sulfate. The solvent was then evaporated to give 7.11 g (96%) of the desired compound as a pale yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer washed sequentially with water and brine
  3. dry with materialwas dried over sodium sulfate
  4. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-1c4ec5195de246b5b7c35a4d35653321
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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