HCID 70237892, compound → HCID 57135689, compound

HRID 565252Notes

Reaction equation

HRID 565252 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]1[C@@H:11]([CH3:12])[C@@H:10]([CH2:13]/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[C:9]1=[O:23]>CO.[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]1[C@@H:11]([CH3:12])[C@@H:10]([CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[C:9]1=[O:23]

Participants

4

Reactant 1

HCID 70237892HCID 70237892, compound

Product 1

HCID 57135689HCID 57135689, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3R,4S)-1-(2-tetrahydropyranyloxy)-3-((2E)-3-(4-methylphenyl)-2-propene-1-yl)-4-methylazetidin-2-one (165 mg, 0.524 mmol) in 4 mL of methanol is treated with 20 mg of 5% palladium on barium sulfate. The resulting suspension is repeatedly evacuated and purged with a hydrogen balloon, then stirred under 1 atmosphere pressure of hydrogen gas for 72 h. The catalyst is filtered and the filtrate is concentrated in vacuo to provide (3R,4S)-1-(2-tetrahydropyranyloxy)-3-(3-(4-methylphenyl)-1-propyl)-4-methylazetidin-2-one as an oil (160 mg, 96% yield).

Workup

  1. customThe resulting suspension is repeatedly evacuated
  2. custompurged with a hydrogen balloon
  3. filtrationThe catalyst is filtered
  4. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-67f5a2a9184b4792ab54407269ca45b2
Source dataset
uspto-grants-2001_01
Patent number
US06172064B2

Reaction notes

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