Ammonium Chloride → 6-Cyclopropyl-8-(4-(trifluoromethyl)phenylsulfonyl)-8-azabicyclo[3.2.1]oct-6-en-3-one

HRID 2061625Notes

Reaction equation

HRID 2061625 reaction equation
Br[CH:2]1[C:8](=[O:9])[CH:7](Br)[CH:6]2[N:11]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:3]1[CH:4]=[C:5]2[CH:25]1[CH2:27][CH2:26]1.[NH4+].[Cl-]>[Cu].[Zn]>[CH:25]1([C:5]2[CH:6]3[N:11]([S:12]([C:15]4[CH:16]=[CH:17][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:19][CH:20]=4)(=[O:14])=[O:13])[CH:3]([CH:4]=2)[CH2:2][C:8](=[O:9])[CH2:7]3)[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 673034852,4-Dibromo-6-cyclopropyl-8-(4-(trifluoromethyl)phenylsulfonyl)-8-azabicyclo[3.2.1]oct-6-en-3-one

Product 1

HCID 673033346-Cyclopropyl-8-(4-(trifluoromethyl)phenylsulfonyl)-8-azabicyclo[3.2.1]oct-6-en-3-oneYield 73%

Reagents, catalysts & solvents 1

HCID 10290809Zinc copper coupleCatalyst

Procedure

Zinc-copper couple (3.21 g, 24.8 mmol) was added to a solution of 2,4-dibromo-6-cyclopropyl-8-(4-(trifluoromethyl)phenylsulfonyl)-8-azabicyclo[3.2.1]oct-6-en-3-one (3.29 g, 6.21 mmol) in a saturated methanolic solution of NH4Cl (24 mL). The reaction mixture was stirred at room temperature for 4 h and was subsequently filtered though Celite. The filtrate was concentrated under vacuum, re-dissolved in CH2Cl2 and washed with saturated aqueous Na2CO3. The organic phase was separated, dried (Na2SO4), filtered, concentrated under vacuum and purified on a silica gel column (eluant hexane/EtOAc, 9/1 to 1/1, v/v) to give compound 116 (1.68 g, 4.52 mmol, 73%). MS (ESI) 372.1 (M+H).

Workup

  1. filtrationwas subsequently filtered though Celite
  2. concentrationThe filtrate was concentrated under vacuum
  3. dissolutionre-dissolved in CH2Cl2
  4. washwashed with saturated aqueous Na2CO3
  5. customThe organic phase was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. custompurified on a silica gel column (eluant hexane/EtOAc, 9/1 to 1/1

Sources & evidence

ORD record
ord-ee825dc5bd4b4cf0a3a12f6ae5550022
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

Loading…