Methanol → 5-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)pentanoic acid

HRID 257739Notes

Reaction equation

HRID 257739 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]C)=[O:12])[CH2:3][CH2:2]1.[OH-:15].[Na+].[CH3:17][OH:18]>OS([O-])(=O)=O.[K+].C(OCC)(=O)C>[C:17]([N:1]1[CH2:2][CH2:3][CH:4]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH2:5][CH2:6]1)([O:18][C:4]([CH3:7])([CH3:5])[CH3:3])=[O:15]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 19781432Methyl 5-(4-piperidyl)pentanoate

Product 1

HCID 107318735-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)pentanoic acid

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516920Potassium bisulfateSolvent

Procedure

A mixture of ester 15 (200 mg, 0.7 mmol), in NaOH (1.0 mL, 1.0 mmol), and CH3OH (4.0 mL) was stirred at ambient temperature for 20 hours. The reaction mixture was then diluted sequentially with 5% KHSO4 and ethyl acetate. The ethyl acetate portion was washed with brine, dried (MgSO4), and concentrated to give the carboxylic acid 16 (190 mg) as a colorless oil.

Workup

  1. washThe ethyl acetate portion was washed with brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b328f86e23db40c196eb691a4832c806
Source dataset
uspto-grants-1993_11
Patent number
US05264420

Reaction notes

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