Methanol → HCID 69686650, compound

HRID 498126Notes

Reaction equation

HRID 498126 reaction equation
[C:1]([O:5][C:6]([C@H:8]1[CH2:10][C@@H:9]1[CH:11]1[CH2:15][CH2:14][N:13](O)[C:12]1=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+]>[Cl-].[Cl-].[Cl-].[Ti+3].O>[C:1]([O:5][C:6]([C@H:8]1[CH2:10][C@@H:9]1[CH:11]1[CH2:15][CH2:14][NH:13][C:12]1=[O:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 23391858HCID 23391858, compound

Product 1

HCID 69686650HCID 69686650, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 962WaterSolvent2×

Procedure

To 100 ml of a solution of 1.85 g of the resulting 3-[(1R,2S)-2-t-butoxycarbonylcyclopropyl]-1-hydroxypyrrolidin-2-one in a 3:1 mixed solvent of methanol and water was added 4.45 ml of a titanium trichloride solution at room temperature while maintaining the reaction mixture neutral by addition of a 1N sodium hydroxide aqueous solution, followed by stirring at the same temperature for 1.5 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give 1.53 g (88.4%) of 3-[(1R,2S)-2-t-butoxycarbonylcyclopropyl]pyrrolidin-2-one.

Workup

  1. temperaturewhile maintaining the reaction mixture
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ae2519d427ae471582389598a37af818
Source dataset
uspto-grants-2005_09
Patent number
US06949662B2

Reaction notes

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