Hydrochloric Acid → HCID 59556879, compound

HRID 1173707Notes

Reaction equation

HRID 1173707 reaction equation
[Si]([O:8][C@H:9]1[C@H:13]([CH3:14])[N:12]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)[C:11](=[O:27])[C:10]1([CH3:29])[CH3:28])(C(C)(C)C)(C)C.CO.Cl.O>O1CCCC1>[OH:8][C@H:9]1[C@H:13]([CH3:14])[N:12]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([C:23]([F:24])([F:25])[F:26])[CH:16]=2)[C:11](=[O:27])[C:10]1([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 59556981HCID 59556981, compound

Product 1

HCID 59556879HCID 59556879, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[(4R,5S)-4-(tert-butyldimethylsilyloxy)-3,3,5-trimethyl-2-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile (391.7 mg) in tetrahydrofuran (12 mL)-methanol (12 mL) was added 6 mol/L hydrochloric acid (12 mL), and the mixture was stirred at room temperature for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1→1/3) to give the title compound as a colorless oil (yield: 203.6 mg, 71%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10/1→1/3)

Sources & evidence

ORD record
ord-d45d794a9023469a84b5fcf8f7a074ce
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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