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

HRID 403511Notes

Reaction equation

HRID 403511 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]>>[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

3

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 acid

Procedure

A 2M aq solution of NaOH (13.5 ml, 27 mmol) was added to a solution of 4-ethoxycarbonylmethyl-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (39) (5.17 g, 18 mmol) at rt. After stirring at rt for 1 h, methanol was evaporated and the residue was treated with water and extracted twice with Et2O, the water layer was then acidified with 2M aq solution of HCl (15 ml), extracted twice with EtOAc and the combined organic layers were dried over Na2 SO4 and concentrated to provide the product as white solid.

Workup

  1. custommethanol was evaporated
  2. additionthe residue was treated with water
  3. extractionextracted twice with Et2O
  4. extractionextracted twice with EtOAc
  5. customthe combined organic layers were dried over Na2 SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-df6a406bae67472f933a108f2185155c
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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