Water → HCID 66661900, compound

HRID 969189Notes

Reaction equation

HRID 969189 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 dryed (over MgSO4), and concentrated to afford the product. LCMS: m/z 370.4 (M+H)+

Workup

  1. extractionwas extracted with AcOEt
  2. concentrationconcentrated
  3. customto afford the product

Sources & evidence

ORD record
ord-44a3d9b3d51d44e2a6b93668abfe709c
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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