Sodium Bicarbonate → 1-Benzyl-3-methyl-4-piperidone

HRID 362547Notes

Reaction equation

HRID 362547 reaction equation
BrCC(N1C[CH2:9][N:8]([C:11](=O)[C:12]2[CH:17]=[C:16](C)[CH:15]=[C:14](C)[CH:13]=2)[CH2:7][CH:6]1[C:21]1[CH:26]=[CH:25]C(Cl)=C(Cl)C=1)=O.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].C([O-])(O)=[O:44].[Na+]>C1COCC1>[CH2:11]([N:8]1[CH2:7][CH2:6][C:21](=[O:44])[CH:26]([CH3:25])[CH2:9]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 3611392Lithium tri-s-butylborohydrideHCID 10277726(+,-)-Bromoacetyl-2-(3,4-dichlorophenyl)-4-(3,5-dimethylbenzoyl)piperazine

Product 1

HCID 5609651-Benzyl-3-methyl-4-piperidone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-23 °C

Procedure

To a cooled solution of compound 3 from step 1 (8.65 g, 34.8 mmol) in THF (100 mL) at -23° C. was added 27.8mL of 1M L-selectride (27.8 mmol). The mixture was stirred at -23° C. for 2 h. After warming to RT, the reaction mixture was added to sat. NaHCO3 and partitioned. The aqueous layer was extracted with Et2O (2×50 mL). The combined organic layers were washed with brine (50 mL), dried with MgSO4 and concentrated. The product was purified by silica gel chromatography eluting with 6:1 to 3:1 hexane-EtOAc to give 2.47 g of compound 4 and 2.75 g of recovered starting material.

Workup

  1. temperatureAfter warming to RT
  2. custompartitioned
  3. extractionThe aqueous layer was extracted with Et2O (2×50 mL)
  4. washThe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customThe product was purified by silica gel chromatography
  8. washeluting with 6:1 to 3:1 hexane-EtOAc

Sources & evidence

ORD record
ord-87320c251b804d9ba066e4037db0201e
Source dataset
uspto-grants-1999_02
Patent number
US05869488

Reaction notes

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