Water → HCID 66661900, compound

HRID 557925Notes

Reaction equation

HRID 557925 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-6d490269bb484bce8e633c6eb6cdcc3c
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

Loading…