1-Benzyloxycarbonyl-3-piperidone → Benzyl 3-hydroxy-3-phenylpiperidine-1-carboxylate

HRID 2177472Notes

Reaction equation

HRID 2177472 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[CH2:20]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[CH2:9]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH2:22][C:21]([OH:25])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:20]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 15141691-Benzyloxycarbonyl-3-piperidoneHCID 178418255HCID 178418255, compound

Product 1

HCID 59438410Benzyl 3-hydroxy-3-phenylpiperidine-1-carboxylateYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 9 ml (9 mmol) phenylmagnesium bromide (1M solution in THF) in THF (13 ml) was added a solution of 1.5 g (6.00 mmol) 3-oxo-piperidine-1-carboxylic acid benzyl ester (commercial) in THF (5 ml) at room temperature over a period of 15 minutes. The mixture was stirred for 30 minutes and then quenched under ice bath cooling with a 20% ammonium chloride solution (4 ml). The organic layer was decanted and the residue was extracted once with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude oil was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 50%) to provide 0.55 g (30%) of the title compound as a white solid. MS (m/e): 312.0 (M+H+)

Workup

  1. customquenched under ice bath
  2. temperaturecooling with a 20% ammonium chloride solution (4 ml)
  3. customThe organic layer was decanted
  4. extractionthe residue was extracted once with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude oil was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 50%)

Sources & evidence

ORD record
ord-a9a5d715e9c14b6294739513fd2c1edb
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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