Lithium hydroxide, monohydrate → HCID 59261041, compound

HRID 643531Notes

Reaction equation

HRID 643531 reaction equation
C([O:4][CH:5]1[CH2:9][CH2:8][C@:7]([CH:26]([CH3:28])[CH3:27])([C:10]([N:12]2[CH2:17][C:16]3[CH:18]=[C:19]([C:22]([F:25])([F:24])[F:23])[CH:20]=[CH:21][C:15]=3[O:14][CH2:13]2)=[O:11])[CH2:6]1)(=O)C.O[Li].O>O.[Cl-].[Na+].O>[CH:26]([C@:7]1([C:10]([N:12]2[CH2:17][C:16]3[CH:18]=[C:19]([C:22]([F:24])([F:25])[F:23])[CH:20]=[CH:21][C:15]=3[O:14][CH2:13]2)=[O:11])[CH2:8][CH2:9][CH:5]([OH:4])[CH2:6]1)([CH3:28])[CH3:27]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59261055HCID 59261055, compound

Product 1

HCID 59261041HCID 59261041, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of (3S)-3-isopropyl-3-{[6-(trifluoromethyl)-2H-1,3-benzoxazin-3(4H)-yl]carbonyl}cyclopentyl acetate (935 mg, 2.34 mmol) was treated with a solution of LiOH H2O (491 mg, 11.7 mmol) in deionized water (5 mL). The resulting reaction mixture was stirred at rt for 40 min, then was diluted with brine and extracted with ether. The ethereal layer was dried over anhydrous MgSO4, filtered, and concentrated to give (3S)-3-isopropyl-3-{[6-(trifluoromethyl)-2H-1,3-benzoxazin-3(4H)-yl]carbonyl}cyclopentanol (a mixture of two isomers), which was used as is.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with ether
  3. dry with materialThe ethereal layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c24748b6869f4064953f6285c8cbbfe0
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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