Tetrabutylammonium Fluoride → Methyl 2-(3,3-dimethylbutyl)-4-(hydroxymethyl)piperidine-1-carboxylate

HRID 1963264Notes

Reaction equation

HRID 1963264 reaction equation
[Si]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH:12]([CH2:20][CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:11]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:23][C:22]([CH3:25])([CH3:24])[CH2:21][CH2:20][CH:12]1[CH2:11][CH:10]([CH2:9][OH:8])[CH2:15][CH2:14][N:13]1[C:16]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66731995Methyl 4-((tert-butyldimethylsilyloxy)methyl)-2-(3,3-dimethylbutyl)piperidine-1-carboxylate

Product 1

HCID 66735064Methyl 2-(3,3-dimethylbutyl)-4-(hydroxymethyl)piperidine-1-carboxylateYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-((tert-butyldimethylsilyloxy)methyl)-2-(3,3-dimethylbutyl)piperidine-1-carboxylate (3.606 g, 9.7 mmol) was dissolved in THF (50 mL) and TBAF (1M in THF) (13 mL, 13 mmol) added. Stirred at room temperature for 3.5 h. The solvent was evaporated. Redissolved in DCM and washed with satd NaHCO3. The organic phase was passed through a phase separator and evaporated to yield an oil. The residue was purified via Biotage (eluent 30-70% EtOAc in heptane) to yield methyl 2-(3,3-dimethylbutyl)-4-(hydroxymethyl)piperidine-1-carboxylate (2.45 g, 98%) as a colourless oil. MS m/z 258 (M+H)+

Workup

  1. customThe solvent was evaporated
  2. dissolutionRedissolved in DCM
  3. washwashed with satd NaHCO3
  4. customevaporated
  5. customto yield an oil
  6. customThe residue was purified via Biotage (eluent 30-70% EtOAc in heptane)

Sources & evidence

ORD record
ord-614501809fc440a9b70d8a3455f707ae
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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