HCID 69558144, compound → HCID 57457968, compound

HRID 1245030Notes

Reaction equation

HRID 1245030 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:13][C@@H:12]1[CH2:22][C:23]#[N:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:13][C@H:12]1[CH2:22][C:23]#[N:24])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 69558144HCID 69558144, compound

Product 1

HCID 57457968HCID 57457968, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.32 g of 20% palladium hydroxide on carbon were added to a solution of 11.60 g (36.4 mmol) of (S)-1-benzyloxycarbonyl-2-cyanomethyl-4-phenyl-3-pyrroline [obtained as described in Preparative Example 6(ii)′ above] in 150 ml of ethyl acetate, and the resulting mixture was stirred for 7 hours at room temperature under a hydrogen atmosphere. At the end of this time, the reaction mixture was filtered and the filtrate was concentrated by evaporation under reduced pressure. The resulting residue was purified by chromatography on a silica gel column using a 4:1 by volume mixture of hexane and ethyl acetate as the eluant to afford 8.18 g (yield: 70%) of the title compound as a pale brown oil.

Workup

  1. customobtained
  2. filtrationAt the end of this time, the reaction mixture was filtered
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  4. customThe resulting residue was purified by chromatography on a silica gel column
  5. additionby volume mixture of hexane and ethyl acetate as the eluant

Sources & evidence

ORD record
ord-b5431d64e94049599fe52d3f80f0bb92
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

Loading…