4-Piperidinecarboxylic acid → 1-Carbobenzoxy-4-piperidinecarboxylic Acid

HRID 2103395Notes

Reaction equation

HRID 2103395 reaction equation
C(N(CC)CC)C.[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>ClCCl>[CH2:21]([O:20][C:18]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 8471TriethylamineHCID 10387Benzyl chloroformate

Product 1

HCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (8.1 mL, 58 mmol) was added to a solution of piperidine-4-carboxylic acid (5 g, 40 mmol) and benzyl chloroformate (7.9 g, 46 mmol) in dichloromethane (100 mL) in an ice-water bath. After being stirred overnight, the solution was washed with concentrated HCl and brine, dried over Na2SO4 and concentrated. Chromatography on silica gel gave the title compound (10 g) as an oil. MS (M+H) 264.2.

Workup

  1. washthe solution was washed with concentrated HCl and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5e0939de426846cabeabdc373a332988
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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