HCID 86740481, compound → HCID 70390872, compound

HRID 653315Notes

Reaction equation

HRID 653315 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-ef027e969dfb4f6ab4f87c61d689d137
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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