Trifluoroacetic acid water → 3-(benzyloxy)piperidin-4-one TFA salt

HRID 43553Notes

Reaction equation

HRID 43553 reaction equation
O.[C:2]([OH:8])([C:4]([F:7])([F:6])[F:5])=[O:3].[CH2:9]([O:16][CH:17]1[C:22](OC)([O:23]C)[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[OH:8][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[CH2:9]([O:16][CH:17]1[C:22](=[O:23])[CH2:21][CH2:20][NH:19][CH2:18]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 22392675Trifluoroacetic acid waterHCID 67505617tert-Butyl 3-(benzyloxy)-4,4-dimethoxypiperidine-1-carboxylate

Product 1

HCID 866485693-(benzyloxy)piperidin-4-one TFA salt

Conditions

Temperature
60 °C

Procedure

A water/TFA mixed solution (1/1, 35 mL) was added to tert-butyl 3-(benzyloxy)-4,4-dimethoxypiperidine-1-carboxylate obtained in Example (90a) (4.99 g, 14.2 mmol), and the mixture was stirred at 60° C. for one hour. The reaction solution was concentrated to obtain crude 3-(benzyloxy)piperidin-4-one TFA salt as a brown oily substance. A 2 N aqueous sodium hydroxide solution (20 mL) was added to the crude 3-(benzyloxy)piperidin-4-one TFA salt, and a solution of di-tert-butyl dicarbonate (4.36 g, 20 mmol) in THF (10 mL) was added at room temperature. Following stirring for one hour, the reaction solution was diluted with water, followed by extraction with ethyl acetate. Then, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=10/1, 5/1, 2/1) to obtain 3.81 g of the title compound as a light brown oily substance (88%).

Workup

  1. concentrationThe reaction solution was concentrated

Sources & evidence

ORD record
ord-1088430b7ae249eb98a43b158cafcef4
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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