HCID 58237949, compound → HCID 58237934, compound

HRID 1192924Notes

Reaction equation

HRID 1192924 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)([CH2:16][CH2:17][CH2:18][OH:19])[CH2:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1.CC(C)=[O:30].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:16][CH2:17][C:18]([OH:30])=[O:19])([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:12][C:11]2=[O:27])[CH3:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 58237949HCID 58237949, compoundHCID 131709961Jones' reagent

Product 1

HCID 58237934HCID 58237934, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-1-((S)-1-(4-bromophenyl)ethyl)-4-(4-fluorophenyl)-4-(3-hydroxypropyl)piperidin-2-one (30 mg, 0.069 mmol) in acetone (2 mL) was added Jones reagent (0.3 mL, 2.5 M) at 0° C. The mixture was stirred for 0.5 h, diluted with EtOAc, and washed with water. The organic phase was concentrated to give the crude 3-((S)-1-((S)-1-(4-bromophenyl)ethyl)-4-(4-fluorophenyl)-2-oxopiperidin-4-yl)propanoic acid (28 mg, 90%), which was used for the next step without further purification.

Workup

  1. washwashed with water
  2. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-9a4a5c5792314995bebae6462e7b81f4
Source dataset
uspto-grants-2014_03
Patent number
US08680281B2

Reaction notes

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