Tetrabutylammonium Fluoride → (1-Benzylpiperidin-2-yl)methanol

HRID 893283Notes

Reaction equation

HRID 893283 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[CH2:32][O:33][Si](C(C)(C)C)(C)C)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:19]([N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[CH2:32][OH:33])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 198919761-Benzyl-2-(tert-butyldimethylsilyloxymethyl)piperidine

Product 1

HCID 2735486(1-Benzylpiperidin-2-yl)methanolYield 62.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled THF solution of tetrabutylammonium fluoride (1M, 3.2 ml) was dropwise added a THF (2 ml) solution of 1-benzyl-2-(tert-butyldimethylsilyloxymethyl)-piperidine (1.00 g, 3.2 mmol). After stirring at room temperature for 2 hours, a reaction solution was poured onto water followed by extraction with ethyl acetate (30 ml). The extract was washed successively with water and saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The crude product thus obtained was purified by a column chromatography on silica gel (SiO2 : 20 g, CHCl3) to afford 0.41 g of the title compound.

Workup

  1. additiona reaction solution was poured onto water
  2. extractionfollowed by extraction with ethyl acetate (30 ml)
  3. washThe extract was washed successively with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe crude product thus obtained
  7. customwas purified by a column chromatography on silica gel (SiO2 : 20 g, CHCl3)

Sources & evidence

ORD record
ord-51054db7224a4378b2d663af651870ed
Source dataset
uspto-grants-1992_06
Patent number
US05124324

Reaction notes

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