Water → HCID 66661900, compound

HRID 2275638Notes

Reaction equation

HRID 2275638 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-221aa333c6924183ac0e5e3146d3dbd5
Source dataset
uspto-grants-2015_09
Patent number
US09126927B2

Reaction notes

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