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Water → 1-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

HRID 50052
Notes
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Reaction equation

HRID 50052 reaction equation
C(N(CC)CC)C.O.[NH:9]1[CH2:17][CH2:16][CH:12]([C:13]([OH:15])=[O:14])[CH2:11][CH2:10]1.[C:18](=O)([O:24]C(C)(C)C)[O:19][C:20]([CH3:23])([CH3:22])[CH3:21]>O1CCOCC1>[C:20]([O:19][C:18]([N:9]1[CH2:17][CH2:16][CH:12]([C:13]([OH:15])=[O:14])[CH2:11][CH2:10]1)=[O:24])([CH3:23])([CH3:22])[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 37734-Piperidinecarboxylic acidHCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidYield 95.8%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Conditions

Temperature
60 °C

Procedure

8.6 g of triethylamine and 20 ml of water are added to a solution of 10 g of isonipecotic acid in 100 ml of dioxane and the mixture is heated to 60° C. 20.25 g of di-tert-butyl carbonate are then added dropwise and the mixture is stirred for 1 hour at 60° C. and refluxed for 30 minutes. It is concentrated under vacuum, the residue is taken up with water and acidified to pH 3 by the addition of 2 N HCl solution and the precipitate formed is filtered off to give 17 g of the expected product.

Workup

  1. temperaturerefluxed for 30 minutes
  2. concentrationIt is concentrated under vacuum
  3. additionacidified to pH 3 by the addition of 2 N HCl solution
  4. customthe precipitate formed
  5. filtrationis filtered off

Sources & evidence

ORD record
ord-2839b4b8535f4f1284e5c5ef0171095d
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06710042B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes