Sodium Hydroxide → 2-{1-[(Tert-butoxy)carbonyl]-4-hydroxypiperidin-4-yl}acetic acid

HRID 1691651Notes

Reaction equation

HRID 1691651 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]([CH2:17][C:18]([O:20]CC)=[O:19])([OH:16])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>O.CO>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH2:12][C:13]([CH2:17][C:18]([OH:20])=[O:19])([OH:16])[CH2:14][CH2:15]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10469302Tert-butyl 4-(2-ethoxy-2-oxoethyl)-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 100611062-{1-[(Tert-butoxy)carbonyl]-4-hydroxypiperidin-4-yl}acetic acidYield 77.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A 2.0 M solution of sodium hydroxide in water (28 mL) was added to a solution of A1 (11.31 g) in methanol (40 mL). The reaction mixture was stirred for 1 h at RT. The organic solvent was removed under a vacuum and the remaining aqueous reaction mixture was repeatedly extracted with ether. The aqueous phase was acidified with 2.0 M hydrochloric acid solution in water and repeatedly extracted with DCM. The combined DCM organic phases were washed with sat. aq. NaCl solution, dried over Na2SO4 and the solvent was removed under a vacuum. 7.9 g of the desired product 4-carboxymethyl-4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (A2) were obtained and further reacted without purification.

Workup

  1. customThe organic solvent was removed under a vacuum
  2. extractionthe remaining aqueous reaction mixture was repeatedly extracted with ether
  3. extractionrepeatedly extracted with DCM
  4. washThe combined DCM organic phases were washed with sat. aq. NaCl solution
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under a vacuum

Sources & evidence

ORD record
ord-bb7a50a9f70a4726b94ef58f5f62c82b
Source dataset
uspto-grants-2012_04
Patent number
US08153795B2

Reaction notes

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