HCID 57528785, compound → HCID 57528735, compound

HRID 1453919Notes

Reaction equation

HRID 1453919 reaction equation
C([O:8][CH2:9][C@H:10]1[CH2:14][NH:13][C:12](=[O:15])[C@@H:11]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)C1C=CC=CC=1>CO.[C].[Pd]>[OH:8][CH2:9][C@H:10]1[CH2:14][NH:13][C:12](=[O:15])[C@@H:11]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 57528785HCID 57528785, compound

Product 1

HCID 57528735HCID 57528735, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

10% Palladium-carbon (1.7 g) was added to a solution of (3S,4R)-4-[(benzyloxy)methyl]-3-phenyltetrahydro-1H-2-pyrrolone (1.73 g, 6.2 mmol) in methanol (40 ml). The mixture was stirred at room temperature under a hydrogen stream for 15 hours and further stirred at 60° C. for 3 hours. The reaction mixture was filtered and was subjected to distillation under reduced pressure. Ether was added to the residue and the precipitates were filtered out to yield the title compound as a white solid (1.05 g). 1H-NMR (CDCl3) δ(ppm) 1.90 (1H, brs), 2.69 (1H, m), 3.32 (1H, dd, J=10.0 Hz, 8.0 Hz), 3.46 (1H, d, J=9.2 Hz), 3.56 (1H, t, J=8.8 Hz), 3.67 (1H, m), 3.75 (1H, m), 6.50 (1H, brs), 7.19-7.30 (3H, m), 7.32-7.38 (2H, m)

Workup

  1. stirringfurther stirred at 60° C. for 3 hours
  2. filtrationThe reaction mixture was filtered
  3. distillationwas subjected to distillation under reduced pressure
  4. additionEther was added to the residue
  5. filtrationthe precipitates were filtered out

Sources & evidence

ORD record
ord-9a05b7480bb44a379658d300013087e7
Source dataset
uspto-grants-2009_01
Patent number
US07476688B2

Reaction notes

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