Dimethylformamide → HCID 67436315, compound

HRID 1663587Notes

Reaction equation

HRID 1663587 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[N:9]2[CH2:13][C@@H:12]([NH:14][C:15](=[O:27])[C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[C@@H:11]([OH:28])[CH2:10]2)=[CH:4][CH:3]=1.[CH3:36]N(C)C=O.CI>C(#N)C.[Ag]=O>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:9]2[CH2:13][C@@H:12]([NH:14][C:15](=[O:27])[C:16]3[CH:17]=[CH:18][C:19]([O:22][C:23]([F:25])([F:26])[F:24])=[CH:20][CH:21]=3)[C@@H:11]([O:28][CH3:36])[CH2:10]2)=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 67435307HCID 67435307, compound

Product 1

HCID 67436315HCID 67436315, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of (3S,4R)-1-[bis-(4-chlorophenyl)methyl]-3-hydroxy-4-[[4-(trifluoromethoxy)benzoyl]amino]pyrrolidine (75.6 mg, an optical isomer of the compound obtained in Example 2) in acetonitrile (8 mL)/dimethylformamide (2 mL) was added successively methyl iodide (233 μL) and silver oxide (216.8 mg) and the mixture was stirred at room temperature for 23 hours. The reaction mixture was filtered through Cerite, washed with acetonitrile and evaporated in vacuo. The crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=4:1→2:1) to give (3S,4R)-1-[bis-(4-chlorophenyl)methyl]-3-methoxy-4-[[4-(trifluoro-methoxy)benzoyl]amino]pyrrolidine (39.5 mg; yield: 51%) as an amorphous powder.

Workup

  1. filtrationThe reaction mixture was filtered through Cerite
  2. washwashed with acetonitrile
  3. customevaporated in vacuo
  4. customThe crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=4:1→2:1)

Sources & evidence

ORD record
ord-dccaeaccc33e4626bc9e8a416d08df32
Source dataset
uspto-grants-2011_10
Patent number
US08034949B2

Reaction notes

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