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

HRID 2405979Notes

Reaction equation

HRID 2405979 reaction equation
C[O:2][C:3]([C:5]1([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4].O.O.[OH-].[Li+].Cl>O1CCOCC1.CO>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C:5]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:3]([OH:4])=[O:2])[CH2:6][CH2:7]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 20664732HCID 20664732, compound

Product 1

HCID 121510204-Benzyl-1-(tert-butoxycarbonyl)piperidine-4-carboxylic acidYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-benzylpiperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (1.772 g, 5.315 mmol) in dioxane (24 ml), methanol (12 ml), and water (12 ml) at room temperature was added lithium hydroxide monohydrate (4.460 g, 106.292 mmol). After stirring at 50° C. for 2 days the solution was acidified to pH 6 using 2M HCl and the resulting white precipitate extracted with diethyl ether (2×100 ml). The organic phases were combined, dried over sodium sulphate and concentrated to dryness to give the acid as a white solid (1.477 g, 87%). LC/MS (LCT): Rt 7.37 [M+H]+ 319.

Workup

  1. extractionthe resulting white precipitate extracted with diethyl ether (2×100 ml)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-04db51b545944a80b68d48c347f607ae
Source dataset
uspto-grants-2014_08
Patent number
US08809336B2

Reaction notes

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