Sodium Hydroxide → 1-Benzyl-3-(hydroxymethyl)piperidin-4-one

HRID 1815827Notes

Reaction equation

[OH:1][CH2:2][CH:3]1[CH2:12][N:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9][C:4]21CCCC2.CB(Br)C.[OH-:24].[Na+]>ClCCl>[CH2:13]([N:11]1[CH2:10][CH2:9][C:4](=[O:24])[CH:3]([CH2:2][OH:1])[CH2:12]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 3.0 gm (11.4 mMol) 6-hydroxymethyl-8-benzyl-8-azaspiro[4,5]decane in 50 mL dichloromethane was cooled to −78° C. and then treated with 2.2 mL (22.8 mMol) dimethylboron bromide dropwise. After stirring at −78° C. for 4 hours, the reaction mixture was treated with 45 mL 1N sodium hydroxide and was allowed to warm to room temperature. The phases were separated and the aqueous phase was extracted well with dichloromethane. The organic phases were combined, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with dichloromethane containing from 0-5% methanol. Fractions containing product were combined and concentrated under reduced pressure to provide 1.1 gm (44%) 1-benzyl-3-hydroxymethyl-4-oxopiperidine.

Workup

temperatureto warm to room temperature
customThe phases were separated
extractionthe aqueous phase was extracted well with dichloromethane
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
washeluting with dichloromethane containing from 0-5% methanol
additionFractions containing product
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-88a43fb60d6c4d8cb07559c7cd3e7ab9
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881733B1

Reaction notes

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