Water → HCID 56673795, compound

HRID 2243199Notes

Reaction equation

HRID 2243199 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:34]=[CH:33][C:10]([CH2:11][N:12]2[CH2:16][C:15]([CH3:18])([CH3:17])[CH:14]([O:19][C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:21]=3)[C:13]2=[O:32])=[CH:9][CH:8]=1.O>ClCCl>[OH:6][C:7]1[CH:34]=[CH:33][C:10]([CH2:11][N:12]2[CH2:16][C:15]([CH3:18])([CH3:17])[CH:14]([O:19][C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([C:28]([F:31])([F:29])[F:30])[CH:21]=3)[C:13]2=[O:32])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 25134Boron tribromideHCID 56673793HCID 56673793, compound2×

Product 1

HCID 56673795HCID 56673795, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (3 eq.) was added dropwise to a −78° C. solution of 4-[1-(4-methoxy-benzyl)-4,4-dimethyl-2-oxo-pyrrolidin-3-yloxy]-2-trifluoromethyl-benzonitrile (220 mg, 1_eq. in dichloromethane, i.e. the product of example 7). The reaction was allowed to gradually warm to ambient temperature overnight. Water was carefully added to the reaction and the product was extracted into dichloromethane. The organic layer was washed with water and brine and dried over anhydrous magnesium sulfate, filtered and concentrated. The crude material was purified by flash column chromatography. (Procedure of example 8 will be referred to as a “demethylation reaction hereinafter”) MS (APCl, M+1) 405.0 LCMS: 50-2% H2O, 214 nm, 2.390 min, 100%

Workup

  1. extractionthe product was extracted into dichloromethane
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash column chromatography
  7. custom(Procedure of example 8 will be referred to as a “demethylation reaction hereinafter”) MS (APCl, M+1) 405.0 LCMS

Sources & evidence

ORD record
ord-9cc575b461694fb68a5a99366584446c
Source dataset
uspto-grants-2010_03
Patent number
US07674819B2

Reaction notes

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