Methyl iodide → HCID 66750656, compound

HRID 504163Notes

Reaction equation

HRID 504163 reaction equation
CI.[CH2:3]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[C:19](=[O:37])[NH:20][C@H:21]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:38](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[CH2:3]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[C:19](=[O:37])[NH:20][C@H:21]([C:30]([O:32][C:33]([CH3:34])([CH3:36])[CH3:35])=[O:31])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:38])=[CH:25][CH:24]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 66750805HCID 66750805, compound

Product 1

HCID 66750656HCID 66750656, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl iodide (4.00 mL, 64.2 mmoles) was added to a room temperature solution of (S)-2-[(S)-1-tert-Butoxycarbonyl-2-(4-hydroxy-phenyl)-ethylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (1.39 g, 2.88 mmoles) and cesium carbonate (1.87 g, 5.75 mmoles) in DMF (10 mL) and the mixture stirred at room temperature for 4 days. The reaction mixture was diluted with EtOAc (200 mL) and washed with brine (3×200 mL). The aqueous layers were re-extracted with EtOAc (2×200 mL). The organic layers were dried (Na2SO4), combined, and concentrated in vacuo to give a yellow oil. Purification of the residue by flash chromatography, eluting with 0-10% EtOAc/CH2Cl2 afforded 0.71 g (50% yield) of (S)-2-[(S)-1-tert-Butoxycarbonyl-2-(4-methoxy-phenyl)-ethylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester, as a colorless oil.

Workup

  1. washwashed with brine (3×200 mL)
  2. extractionThe aqueous layers were re-extracted with EtOAc (2×200 mL)
  3. dry with materialThe organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give a yellow oil
  6. customPurification of the residue by flash chromatography
  7. washeluting with 0-10% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-1e4f02504e484f51bb104c16bd86473c
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

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