3,3-Diphenyl-3,4,5,6-tetrahydropyridin-2-ol → HCID 4341835, compound

HRID 1667087Notes

Reaction equation

HRID 1667087 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][CH2:10][NH:9][C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 3211653,3-Diphenyl-3,4,5,6-tetrahydropyridin-2-olHCID 21226445Aluminium lithium hydride

Product 1

HCID 4341835HCID 4341835, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 500 mL flask containing 3,3-diphenylpiperidin-2-one (3.77 g, 15 mmol; Example 68C) as a suspension in ether (300 mL) was added lithium aluminum hydride (2.0 Min tetrahydrofuran, 15 mL, 30 mmol) slowly via syringe under nitrogen. The reaction was refluxed overnight, cooled to room temperature, and then carefully quenched by the slow addition of 1 N NaOH (60 mL). The reaction was diluted with ethyl acetate (200 mL) and filtered through a pad or diatomaceous earth. The organic phase was separated, concentrated, and the residue was purified over silica gel eluting with 95:5 dichloromethane/methanol to give the title compound. MS (DCI+) m/z 238 (M+H)+.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. customcarefully quenched by the slow addition of 1 N NaOH (60 mL)
  3. additionThe reaction was diluted with ethyl acetate (200 mL)
  4. filtrationfiltered through a pad or diatomaceous earth
  5. customThe organic phase was separated
  6. concentrationconcentrated
  7. customthe residue was purified over silica gel eluting with 95:5 dichloromethane/methanol

Sources & evidence

ORD record
ord-47e5b4a80f86482cb9f3e27d60caedf1
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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