HCID 86740481, compound → HCID 70390872, compound

HRID 2231598Notes

Reaction equation

HRID 2231598 reaction equation
[C:1]1(=[O:35])[N:5]([C@H:6]2[C@@H:9](/[CH:10]=[CH:11]/[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=3[O:27][CH3:28])[C:7]2=[O:29])[C:4](=[O:30])[C:3]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:2]12.[H][H]>O1CCCC1.[Pd]>[C:4]1(=[O:30])[N:5]([C@H:6]2[C@@H:9]([CH2:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:8]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=3[O:27][CH3:28])[C:7]2=[O:29])[C:1](=[O:35])[C:2]2=[CH:34][CH:33]=[CH:32][CH:31]=[C:3]12

Participants

5

Reactant 2

HCID 86740481HCID 86740481, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70390872HCID 70390872, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In 150 ml of tetrahydrofuran is dissolved 5 g of cis-3-phthalimido-4-(E)-styryl-1-(2,4-dimethoxybenzyl)-2-oxoazetidine, followed by addition of 2.5 g of 10% palladium-on-carbon. The mixture is stirred in a hydrogen atmosphere for 30 minutes. The catalyst is filtered off and the filtrate is concentrated under reduced pressure. The residue is crystallized from ether and recovered by filtration to give 4.8 g of cis-3-phthalimido-4-(2-phenylethyl)-1-(2,4-dimethoxybenzyl)-2-oxoazetidine, m.p. 148°-150° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is crystallized from ether
  4. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-87d5b9fdaba54571b134f79555daf41c
Source dataset
uspto-grants-1988_11
Patent number
US04782147

Reaction notes

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