HCID 67469775, compound → HCID 67469906, compound

HRID 407915Notes

Reaction equation

HRID 407915 reaction equation
C([O:8][C@H:9]1[CH2:13][N:12]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[C:11](=[O:27])[C@H:10]1[O:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][C:30]=1[F:39])C1C=CC=CC=1.[H][H]>CCO.[Pd]>[F:39][C:30]1[CH:31]=[C:32]([S:35]([CH3:38])(=[O:37])=[O:36])[CH:33]=[CH:34][C:29]=1[O:28][C@H:10]1[C@@H:9]([OH:8])[CH2:13][N:12]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[C:11]1=[O:27]

Participants

5

Reactant 2

HCID 67469775HCID 67469775, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67469906HCID 67469906, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Tert-butyl 4-((3S,4S)-4-(benzyloxy)-3-(2-fluoro-4-(methylsulfonyl)phenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (160 mg, 0.284 mmol) was dissolved in EtOH (3 mL) and 100 mg 10% Pd/C was added and stirred under balloon pressure of hydrogen overnight. The reaction was filtered and concentrated to afford tert-butyl 4-((3S,4S)-3-(2-fluoro-4-(methylsulfonyl)phenoxy)-4-hydroxy-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (80 mg, 0.169 mmol, 59.5% yield).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-957ffcc75700413ea6296c34cd83a1cc
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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