Tetrabutylammonium Fluoride → (5S)-5-(Hydroxymethyl)-1-methyl-2-pyrrolidinone

HRID 497071Notes

Reaction equation

HRID 497071 reaction equation
[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][C@H:28]1[N:32]([CH3:33])[C:31](=[O:34])[CH2:30][CH2:29]1)(C(C)(C)C)(C)C>C1COCC1>[OH:26][CH2:27][C@H:28]1[N:32]([CH3:33])[C:31](=[O:34])[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18639170(5S)-5-[(tert-butyldimethylsilyloxy)methyl]-1-methylpyrrolidin-2-one

Product 1

HCID 14876039(5S)-5-(Hydroxymethyl)-1-methyl-2-pyrrolidinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Bu4NF (1 mol THF solution, 17.5 ml, 17.5 mmols) was added to a THF (100 ml) solution of the (5S)-5-[(tert-butyldimethylsilyloxy)methyl]-1-methylpyrrolidin-2-one (3.84 g, 15.8 mmols), and the mixture was stirred for 15 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and then the residue was subjected to silica gel column chromatography (SiO2 150 g, MeOH—CHCl3 1:9 v/v) to obtain (5S)-5-(hydroxymethyl)-1-methylpyrrolidin-2-one as a mixture (2.46 g) with inseparable impurities.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b498f257915f4d9c97597204d92e3915
Source dataset
uspto-grants-2005_09
Patent number
US06949553B2

Reaction notes

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