Sodium Hydroxide → 3-[4-(N-BOC-Hydroxypiperidin-4-yl)phenyl]butyric Acid

HRID 265874Notes

Reaction equation

HRID 265874 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]([CH3:27])[CH2:21][C:22]([O:24]CC)=[O:23])=[CH:16][CH:15]=2)[CH2:10][CH:9]1[OH:28])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+].OS([O-])(=O)=O.[K+]>CO>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[CH:16][C:17]([CH:20]([CH3:27])[CH2:21][C:22]([OH:24])=[O:23])=[CH:18][CH:19]=2)[CH2:10][CH:9]1[OH:28])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 19034119Ethyl 3-[4-(N-BOC-hydroxypiperidin-4-yl)phenyl]butyrate

Product 1

HCID 190341203-[4-(N-BOC-Hydroxypiperidin-4-yl)phenyl]butyric Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 12-2 (400 mg, 1.0 mmoles), 1N NaOH (4 mL, 4.0 mmoles), and CH3OH (5 mL) was stirred at ambient temperature for 4.0 hours. The reaction mixture was acidified with 10% KHSO4 and then extracted with EtOAc (2×). The combined extracts were washed with brine, dried (MgSO4), and then concentrated to give 12-3 as a white solid. Rf 0.66 (silica, 10/0.5/0.5 CH2Cl2 /CH3OH/HOAc).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ef25e03b389f4094a21db63e41c41d5f
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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