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

HRID 69923Notes

Reaction equation

HRID 69923 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1.[CH3:18][Mg+].[Br-]>C1COCC1>[OH:1][C:2]1([CH3:18])[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1

Participants

4

Reactant 2

HCID 15141691-Benzyloxycarbonyl-3-piperidoneHCID 178418689HCID 178418689, compound

Product 1

HCID 10634355Benzyl 3-hydroxy-3-methylpiperidine-1-carboxylateYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of benzyl 3-oxopiperidine-1-carboxylate (2.33 g, 10 mmol) in dry THF (50 mL) at −78° C. was added MeMgBr (3.6 mL, 3M solution in THF, 11 mmol) slowly. The reaction was allowed to stir at −78° C. for 10 min then slowly warmed to r.t. The reaction was quenched with NH4Cl and dissolved in EtOAc (300 mL) and washed with saturated NH4Cl and brine, dried and filtered, and concentrated to give the crude. The crude material was further purified by silica gel chromatography to yield benzyl 3-hydroxy-3-methylpiperidine-1-carboxylate. (53% yield). LCMS (m/z): 250.1 (MH+); LC Rt=2.98 min.

Workup

  1. temperaturethen slowly warmed to r.t
  2. customThe reaction was quenched with NH4Cl
  3. dissolutiondissolved in EtOAc (300 mL)
  4. washwashed with saturated NH4Cl and brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude
  9. customThe crude material was further purified by silica gel chromatography

Sources & evidence

ORD record
ord-2e57a71f02f14ccc9ead6aee6a9c6ddc
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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