Toluene → 3-Carbomethoxy-1,3-dibenzyl-4-piperidone

HRID 362545Notes

Reaction equation

HRID 362545 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([C:15]([O:17][CH3:18])=[O:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:29]1([CH3:35])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(Br)C1C=CC=CC=1>C1COCC1>[C:15]([C:10]1([CH2:35][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:11](=[O:14])[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9]1)([O:17][CH3:18])=[O:16]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7498Benzyl BromideHCID 107480Methyl 1-benzyl-4-oxo-3-piperidinecarboxylateHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 542328573-Carbomethoxy-1,3-dibenzyl-4-piperidoneYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-benzyl-3-carbomethoxy-4-piperidone (1.0 g, 4.0 mmol) in THF (10 mL) was treated with 0.5M potassium bis(trimethylsilyl)amide in toluene (9.6 mL, 4.8 mmol) for 15 min, followed by the addition of benzyl bromide (1.2 g, 4.8 mmol). After 2 h, the reaction mixture was quenched with sat. NH4Cl and extracted with ether. The combined organic layers were washed with brine, dried with MgSO4 and concentrated. The product was purified by silica gel chromatography eluting with 4:1 hexane-EtOAc to give 3-carbomethoxy-1,3-dibenzyl-4-piperidone (0.61 g) as a light yellow oil.

Workup

  1. customthe reaction mixture was quenched with sat. NH4Cl
  2. extractionextracted with ether
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe product was purified by silica gel chromatography
  7. washeluting with 4:1 hexane-EtOAc

Sources & evidence

ORD record
ord-ac1f946a108e4de2ad0dcf496383a272
Source dataset
uspto-grants-1999_02
Patent number
US05869488

Reaction notes

Loading…