Water → HCID 66661900, compound

HRID 504388Notes

Reaction equation

HRID 504388 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][C@@H:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C@H:15]([C:24]([O:26]C)=[O:25])[CH2:14]3)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O1CCCC1.[OH-].[Li+].O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]([N:13]3[CH2:17][C@@H:16]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C@H:15]([C:24]([OH:26])=[O:25])[CH2:14]3)=[O:12])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 66661751HCID 66661751, compound

Product 1

HCID 66661900HCID 66661900, compound

Procedure

To a solution of methyl (3S,4R)-1-{[1-(4-chlorophenyl)cyclopropyl]carbonyl}-4-phenylpyrrolidine-3-carboxylate (50 mg, 0.0001 mol, example 39) in tetrahydrofuran (2 mL, 0.02 mol) was added lithium hydroxide (9.4 mg, 0.00039 mol) and water (0.5 mL, 0.03 mol) and the solution was stirred at rt for 1 h. The reaction mixture was then acidified (pH ˜2) and was extracted with AcOEt. The organic layer was dried (over MgSO4), and concentrated to afford the product. LCMS: m/z 370.4 (M+H)+

Workup

  1. extractionwas extracted with AcOEt
  2. dry with materialThe organic layer was dried (over MgSO4)
  3. concentrationconcentrated
  4. customto afford the product

Sources & evidence

ORD record
ord-a5e2275d45e343208d241cab3dd826c6
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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