Water → 1-Benzyl-4-methylpiperidin-4-ol

HRID 2085396Notes

Reaction equation

HRID 2085396 reaction equation
[CH3:1][Li].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>CCOCC>[CH2:3]([N:10]1[CH2:15][CH2:14][C:13]([CH3:1])([OH:16])[CH2:12][CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 192201-Benzyl-4-piperidoneHCID 178418348HCID 178418348, compound

Product 1

HCID 108459131-Benzyl-4-methylpiperidin-4-olYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Methyllithium (1.4 M in Et2O, 54.0 mL) was added to a solution of 1-benzyl-4-piperidone (5.00 mL, 27.0 mmol) in anhydrous ether at −78° C. under argon. Stirring was continued at −78° C. for 1.5 hours. Ether (200 mL) and water (40 mL) were added, and the two phases were separated. The aqueous solution was extracted with Et2O (3×50 mL). The combined organic solutions were dried over magnesium sulfate and concentrated. The residue was chromatographed (EtOAc to EtOAc-MeOH 9/1), giving 4.81 g (87%) of the desired product as a colorless oil: 1H NMR δ 1.21 (s, 3 H), 1.56 (dt, J=13, 3 Hz, 2 H), 1.65 (td, J=10, 4 Hz, 2 H), 2.35 (td, J=10, 3 Hz, 2 H), 2.53 (m, 2 H), 7.24 (m, 1 H), 7.29 (m, 4 H); 13C NMR δ 30.44, 39.37, 50.39, 63.80, 68.50, 127.56, 128.80, 129.80, 139.17.

Workup

  1. customthe two phases were separated
  2. extractionThe aqueous solution was extracted with Et2O (3×50 mL)
  3. dry with materialThe combined organic solutions were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed (EtOAc to EtOAc-MeOH 9/1)

Sources & evidence

ORD record
ord-01be8d6843d846609601331ca77dda3e
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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