Water → HCID 45925980, compound

HRID 577753Notes

Reaction equation

HRID 577753 reaction equation
[F:1][C:2]([F:21])([F:20])[C@@H:3]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][C@H:4]1[C:15]([O:17]CC)=[O:16].[Li+].[OH-].O.C1COCC1>CO>[C:11]([O:10][C:8]([N:6]1[CH2:7][C@@H:3]([C:2]([F:21])([F:1])[F:20])[C@H:4]([C:15]([OH:17])=[O:16])[CH2:5]1)=[O:9])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 131732869HCID 131732869, compound

Product 1

HCID 45925980HCID 45925980, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of trans-1-tert-butyl 3-ethyl 4-(trifluoromethyl)pyrrolidine-1,3-dicarboxylate (61.2 g, 0.19 mol), LiOH (39.9 g, 0.95 mol) in a mixed solvent of water (300 mL), THF (300 mL) and MeOH (150 mL) was stirred at rt overnight. The reaction mixture was concentrated in vacuum, then acidified with 1N HCl to pH=1, and extracted with EtOAc (three×300 mL). The combined organics were dried over Na2SO4 and concentrated to give the title compound (47 g, 87% yield) as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuum
  2. extractionextracted with EtOAc (three×300 mL)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7e31d69520ac489297ff931eb718e5e3
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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