Cyclohexene → HCID 87357620, compound

HRID 1434882Notes

Reaction equation

HRID 1434882 reaction equation
C([O:8][C@@H:9]1[C@@:13]2([CH2:20][O:21][C@H:10]1[C@H:11]([N:22]1[CH:29]=[C:28]([CH3:30])[C:26](=[O:27])[NH:25][C:23]1=[O:24])[O:12]2)[CH2:14][O:15][S:16]([CH3:19])(=[O:18])=[O:17])C1C=CC=CC=1.C1CCCCC=1>[OH-].[OH-].[Pd+2].C(O)C>[S:16]([O:15][CH2:14][C@@:13]12[CH2:20][O:21][C@@H:10]([C@H:11]([N:22]3[CH:29]=[C:28]([CH3:30])[C:26](=[O:27])[NH:25][C:23]3=[O:24])[O:12]1)[C@@H:9]2[OH:8])([CH3:19])(=[O:17])=[O:18]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 11812196HCID 11812196, compound

Product 1

HCID 87357620HCID 87357620, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent2×

Procedure

An ethanol solution of Compound 2 (35 mg, 0.080 mmol) and cyclohexene (0.3 ml, 3.0 mmols) were added to an ethanol suspension of 30 mg of 20% Pd(OH)2/C, and the mixture was heated under reflux for 2 hours. The catalyst was removed by filtration, and the solvent was distilled off under reduced pressure. Then, the resulting 5′-O-mesyl-5-methyl-2′-O,4′-C-methyleneuridine (Compound 3) obtained as a white solid (27 mg) was used for the next reaction without being purified.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customThe catalyst was removed by filtration
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-088e8eb244a543969aa671be7570b4ff
Source dataset
uspto-grants-2009_11
Patent number
US07615619B2

Reaction notes

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