Tetrabutylammonium Fluoride → HCID 28351502, compound

HRID 2368928Notes

Reaction equation

HRID 2368928 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([CH3:15])[CH2:10]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:15][C@@H:11]1[CH2:12][CH2:13][CH2:14][N:9]([CH2:8][CH2:7][OH:6])[CH2:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86682903HCID 86682903, compound

Product 1

HCID 28351502HCID 28351502, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-methyl-piperidine (500 mg, 1.9 mmol) in THF (5 mL) at 0° C., TBAF (1M in THF, 2.8 mL) was slowly added. The reaction mixture was stirred at room temperature for 2 h and concentrated. The residue was purified by silica gel column chromatography (MeOH/CH2Cl2=1/50) to give (R)-2-(3-methyl-piperidin-1-yl)-ethanol (0.23 g) as colorless oil. 1H NMR (DMSO-d6): δ 4.39 (br s, 1H), 3.48 (t, 2H), 2.80-2.77 (m, 2H), 2.38 (t, 2H), 1.88-1.86 (m, 1H), 1.65-1.47 (m, 5H), 0.81 (d, 3H), 0.82-0.78 (m, 1H); LCMS: 144.1 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel column chromatography (MeOH/CH2Cl2=1/50)

Sources & evidence

ORD record
ord-4e1973c58818440abb4d303d56177065
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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