Water → HCID 67436302, compound

HRID 1663583Notes

Reaction equation

HRID 1663583 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[N:9]2[CH2:13][CH2:12][C@@H:11]([NH2:14])[CH2:10]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:29][C:30]([F:42])([F:41])[O:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1.O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[N:9]2[CH2:13][CH2:12][C@@H:11]([NH:14][C:36](=[O:37])[C:35]3[CH:39]=[CH:40][C:32]([O:31][C:30]([F:29])([F:41])[F:42])=[CH:33][CH:34]=3)[CH2:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 11551517HCID 11551517, compound

Product 1

HCID 67436302HCID 67436302, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3R)-1-[bis-(4-chlorophenyl)methyl]-3-aminopyrrolidine (2.05 g, compound obtained in Reference Example 11) and triethylamine (1.35 mL) in methylene chloride (30 mL) was added dropwise 4-(trifluoromethoxy)benzoyl chloride (1.21 mL) under ice-cooling and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added water and the mixture is extracted with chloroform (×2). The organic layer was filtered through a NH-silica gel (10 g of Chromatorex NH-silica gel; Fuji Silicia Chem.) and the filtrate was evaporated in vacuo. The crude product was triturated in ethyl acetate/hexane to obtain (3R)-1-[bis-(4-chlorophenyl)methyl]-3-[[4-(trifluoromethoxy)benzoyl]amino]pyrrolidine (2.70 g; yield: 83%) as crystals.

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform (×2)
  3. filtrationThe organic layer was filtered through a NH-silica gel (10 g of Chromatorex NH-silica gel; Fuji Silicia Chem.)
  4. customthe filtrate was evaporated in vacuo
  5. customThe crude product was triturated in ethyl acetate/hexane

Sources & evidence

ORD record
ord-c60967ec8de543a1a6dd28e27f6b0000
Source dataset
uspto-grants-2011_10
Patent number
US08034949B2

Reaction notes

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