Sodium Hydroxide → HCID 59652047, compound

HRID 221842Notes

Reaction equation

HRID 221842 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[CH:22]([CH3:29])[CH2:23][C:24]([O:26]CC)=[O:25])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([C:21](=[O:30])[CH:22]([CH3:29])[CH2:23][C:24]([OH:26])=[O:25])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59652055HCID 59652055, compound

Product 1

HCID 59652047HCID 59652047, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 4-[4-(3-ethoxycarbonyl-2-methyl-propionyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (Example 189 step 2) (5.7 g, 14 mmol) and 1N NaOH (18 mL) in methanol was heated at 65° C. for 1 h. Methanol was evaporated at reduced pressure and diluted with water then cooled to 0° C. The aqueous layer was neutralized carefully with citric acid and extracted twice with methylene chloride to obtain a crude 4-[4-(3-carboxy-2-methyl-propionyl)phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (4.3 g, 81%), MS m/z 390 (M−1)

Workup

  1. customMethanol was evaporated at reduced pressure
  2. additiondiluted with water
  3. temperaturethen cooled to 0° C
  4. extractionextracted twice with methylene chloride

Sources & evidence

ORD record
ord-d759df8f639c40ccb17e5ce4735eb236
Source dataset
uspto-grants-2012_06
Patent number
US08207168B2

Reaction notes

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