Water → (RS,SR)-2-benzenesulfonyl-2-(3-oxo-cyclohexyl)-propionic acid methyl ester

HRID 602741Notes

Reaction equation

HRID 602741 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH2:6]1.[H-].[Na+].[CH3:24]I.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:21])[C:4]([S:12]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:13])=[O:14])([CH:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH2:6]1)[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11088194Benzenesulfonyl-(3-oxo-cyclohexyl)-acetic acid methyl ester

Product 1

HCID 67266871(RS,SR)-2-benzenesulfonyl-2-(3-oxo-cyclohexyl)-propionic acid methyl esterYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2 g (6.44 mmol) of benzenesulfonyl-(3-oxo-cyclohexyl)-acetic acid methyl ester in 40 mL of DMF at 0° C., 283 mg (7.09 mmol, 1.1 eq) of NaH (60%) were added. The reaction mixture was stirred at this temperature for one hour, and 1.37 g (9.66 mmol, 1.5 eq) of methyliodide were added. After 2 hours at RT, the reaction mixture was poured into water and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. The resulting two diastereomers were separated by column chromatography on silica gel with heptane/EtOAc 2:1, yielding 0.79 g (38%) of (RS,SR)-2-benzenesulfonyl-2-(3-oxo-cyclohexyl)-propionic acid methyl ester as a white solid, MS: 325 (MH+) and 0.71 g (34%) of (RR,SS)-2-benzenesulfonyl-2-(3-oxo-cyclohexyl)-propionic acid methyl ester as a white solid, MS: 325 (MH+).

Workup

  1. waitAfter 2 hours at RT
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting two diastereomers were separated by column chromatography on silica gel with heptane/EtOAc 2:1

Sources & evidence

ORD record
ord-65a9a566e9764b98b5c1c1684bb7e497
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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