Methyl iodide → (RS,SR)-2-(naphthalene-1-sulfonyl)-2-(3-oxocyclohexyl)-propionic acid methyl ester

HRID 602753Notes

Reaction equation

HRID 602753 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH:4]([S:12]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[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+].[CH3:28]I>CN(C=O)C>[CH3:1][O:2][C:3](=[O:25])[C:4]([S:12]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)(=[O:13])=[O:14])([CH:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH2:6]1)[CH3:28]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67266832(Naphthalene-1-sulfonyl)-(3-oxo-cyclohexyl)-acetic acid methyl ester

Product 1

HCID 67266852(RS,SR)-2-(naphthalene-1-sulfonyl)-2-(3-oxocyclohexyl)-propionic acid methyl esterYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to example 3.1:1.74 g (4.8 mmol) of (naphthalene-1-sulfonyl)-(3-oxo-cyclohexyl)-acetic acid methyl ester was dissolved in 10 mL of DMF at 0° C. 232 mg (5.3 mmol, 1.1 eq) of NaH (60%) were added and the reaction mixture was stirred 30 minutes before the addition of 1.03 g (7.2 mmol, 1.5 eq) of methyliodide. The reaction was stirred over night, poured on 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 AcOEt/heptane 2:1, yielded 0.30 g (17%) of (RS,SR)-2-(naphthalene-1-sulfonyl)-2-(3-oxocyclohexyl)-propionic acid methyl ester as a white foam MS: 375 (MH+) and 0.42 g (23%) of (RR,SS)-2-(naphthalene-1-sulfonyl)-2-(3-oxocyclohexyl)-propionic acid methyl ester as a white solid MS: 375 (MH+).

Workup

  1. additionpoured on water
  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 AcOEt/heptane 2:1

Sources & evidence

ORD record
ord-6c5fec2131004868856d6a8f9ec2d5d2
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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