Lithium Hydroxide → HCID 131727566, compound

HRID 2100566Notes

Reaction equation

HRID 2100566 reaction equation
[CH:1]([O:4][C:5]([C:7]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:10]=[CH:9][C:8]=1[C@H:17]1[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19][C@H:18]1[C:29]([O:31]C)=[O:30])=[O:6])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O>[C:25]([O:24][C:22]([N:20]1[CH2:21][C@H:17]([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([C:13]([F:15])([F:16])[F:14])[C:7]=2[C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[O:6])[C@H:18]([C:29]([OH:31])=[O:30])[CH2:19]1)=[O:23])([CH3:26])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 131727565HCID 131727565, compound

Product 1

HCID 131727566HCID 131727566, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of (±)-cis-1-tert-butyl 3-methyl 4-(2-(isopropoxycarbonyl)-3-(trifluoromethyl)phenyl)pyrrolidine-1,3-dicarboxylate (0.90 g, 1.96 mmol) in 20 mL of 2:1 THF/H2O was added lithium hydroxide (52 mg, 2.15 mmol). The reaction mixture was allowed to stir at ambient temperature for 2 h. The reaction was partitioned between 1:1 hexane/EtOAc and dilute aq Na2CO3. The organic layer was discarded. The aqueous layer was acidified with 12 N HCl and extracted with EtOAc. The EtOAc layer was washed with brine, dried (MgSO4) and concentrated to afford 0.75 g (86%) of the title compound as a white foam, which was pure enough to be used without purification. LRMS (ES)+: 446 (M+H)+.

Workup

  1. customThe reaction was partitioned between 1:1 hexane/EtOAc and dilute aq Na2CO3
  2. extractionextracted with EtOAc
  3. washThe EtOAc layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-49ecae3c0a3e47c28a60d316e5d3d33e
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

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