Methyl iodide → HCID 66743543, compound

HRID 656322Notes

Reaction equation

HRID 656322 reaction equation
[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][Si](C)(C)[N-][Si](C)(C)C.[Li+].CCCCCC.CI>O1CCCC1>[CH3:21][C:12]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:13][CH2:14][CH2:15][N:10]([S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])[CH2:11]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 2733832Lithium HexamethyldisilazideHCID 2904534Ethyl 1-(phenylsulfonyl)piperidine-3-carboxylate

Product 1

HCID 66743543HCID 66743543, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At r.t., to the solution of ethyl 1-(phenylsulfonyl)piperidine-3-carboxylate (0.50 g, 2.0 mmol) in tetrahydrofuran (5.0 mL), was slowly added 1.0 M of lithium hexamethyldisilazide in hexane (2.5 mL, 2.5 mmol) with stirring. After stirring for 30 min, to the mixture was added methyl iodide (157 ul, 2.5 mmol). The mixture was stirred at r.t. overnight and was quenched with 10% citric acid, then extracted with ethyl acetate. The extract was washed with water, sat'd sodium bicarbonate solution, water, and brine, successively. The extract was then dried over sodium sulfate (anhydrous). After filtration, the filtrate was concentrated to yield 200 mg (40%) of ethyl 3-methyl-1-(phenylsulfonyl)piperidine-3-carboxylate.

Workup

  1. customAt r.t.
  2. stirringAfter stirring for 30 min, to the mixture
  3. stirringThe mixture was stirred at r.t. overnight
  4. customwas quenched with 10% citric acid
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialThe extract was then dried over sodium sulfate (anhydrous)
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d5a6b5fa09d24325898d42bf943421e0
Source dataset
uspto-grants-2011_12
Patent number
US08071624B2

Reaction notes

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