Tetrahydrofuran → 1-Benzyl-4-methylpiperidin-4-ol

HRID 1167701Notes

Reaction equation

HRID 1167701 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]1COCC1>>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:15])([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 192201-Benzyl-4-piperidone

Product 1

HCID 108459131-Benzyl-4-methylpiperidin-4-olYield 59%

Procedure

To a solution of 1-benzyl-4-piperidone (5.6 mL, 30.0 mmol) in 50 mL THF was added a solution of methyl]ithium in THF (24.0 mL, 36 mmol) dropwise at 0° C. over 15 min. The reaction mixture was allowed to warm to room temperature over 3 h and then quenched with 30 mL of sat. NH4Cl solution. The organic layer was extracted with diethyl ether (2×100 mL) and the combined organic layer was washed with brine (100 mL). The organic layer was separated, dried over Na2SO4, filtered and the solvent was removed in vacuo to obtain yellow gum. It was purified by column chromatography over silica gel with 9:1 EtOAc-MeOH as the eluting system to obtain 1-benzyl-4-methyl-4-piperidinol as a yellow thick oil (3.6 g, 59% yield).

Workup

  1. customquenched with 30 mL of sat. NH4Cl solution
  2. extractionThe organic layer was extracted with diethyl ether (2×100 mL)
  3. washthe combined organic layer was washed with brine (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customto obtain yellow gum
  9. customIt was purified by column chromatography over silica gel with 9:1 EtOAc-MeOH as the eluting system

Sources & evidence

ORD record
ord-e1e2b69755d64e40ad172a0b05cc4f0f
Source dataset
uspto-grants-2003_09
Patent number
US06620815B1

Reaction notes

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