Potassium Bicarbonate → HCID 21193294, compound

HRID 1068485Notes

Reaction equation

HRID 1068485 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:22][O:23][CH3:24])([S:14][C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:25]OS([O-])=O.[K+].C(=O)(O)[O-].[K+]>C(#N)C.O.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH2:22][O:23][CH3:24])([S:14]([C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)=[O:25])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 516893Potassium BicarbonateHCID 21193209HCID 21193209, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 21193294HCID 21193294, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-tert-Butoxycarbonyl-4-methoxymethyl-4-(3-tolylsulfanyl)piperidine (0.26 g, 0.73 mmol; Example 107, Step A) in acetonitrile (10 mL) was treated with a solution of Oxone (0.99 g, 1.6 mmol) in water (10 mL) and potassium bicarbonate (0.56 g, 5.6 mmol) in water (10 mL), and stirred at room temp. for 1 h. The reaction mixture was diluted with dichloromethane and water. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 25% ethyl acetate in hexane. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. extractionThe organic extract
  2. washwas washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-91cb8f0612e74bb098a27a6b50926b7e
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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