Benzyl Bromide → 4-Benzyl-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid

HRID 380656Notes

Reaction equation

HRID 380656 reaction equation
C([O:3][C:4]([C:6]1([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])C.C(Br)C1C=CC=CC=1.[OH-].[Na+].S([O-])(O)(=O)=O.[Na+]>C(O)C.O>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][C:6]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 516919Sodium BisulfateHCID 162182711-tert-Butyl 4-ethyl 4-benzylpiperidine-1,4-dicarboxylate

Product 1

HCID 121510204-Benzyl-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-tert-butyloxycarbonyl-4-benzylpiperidine-4-carboxylic acid ethyl ester (prepared as in Gilligan et al J. Med. Chem. 1994, 364-370 using benzyl bromide as the alkylating agent) (11.0 g; 32 mmol) was refluxed for 7 h. in a mixture of ethanol (190 ml) and aqueous sodium hydroxide (18% 190 ml). The volume was reduced to a third in vacuo and pH was adjusted to 3 with sodium hydrogen sulfate. Water (300 ml) was added and the mixture was extracted with ethylacetate (2×250 ml). The combined organic phases were evaporated to afford 8.6 g of N-tert-butyloxycarbonyl-4-benzylpiperidine-4-carboxylic acid.

Workup

  1. extractionthe mixture was extracted with ethylacetate (2×250 ml)
  2. customThe combined organic phases were evaporated

Sources & evidence

ORD record
ord-744c36590e1e4c2daeb9181001ad04e3
Source dataset
uspto-grants-2001_10
Patent number
US06303620B1

Reaction notes

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