HCID 10674037, compound → HCID 10697467, compound

HRID 274005Notes

Reaction equation

HRID 274005 reaction equation
[CH:1]1([S:7][CH:8]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=2)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([N:15]2[CH2:24][CH2:23][C:22]3[C:17](=[CH:18][C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[CH:21]=3)[CH2:16]2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>O1CCCC1>[CH:1]1([S:7][CH:8]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:15]2[CH2:24][CH2:23][C:22]3[C:17](=[CH:18][C:19]([O:27][CH3:28])=[C:20]([O:25][CH3:26])[CH:21]=3)[CH2:16]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 10674037HCID 10674037, compound

Product 1

HCID 10697467HCID 10697467, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.959 g of 2-[6-(cyclohexylthio)-6-(3,4-dimethoxyphenyl)-1-oxohexyl]-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline and 0.35 mL of borane-methylsulfide complex (10M) in 10 mL of tetrahydrofuran is heated under reflux for 2 hour, cooled and quenched with methyl alcohol. The volatiles are removed in vacuo. The residue is taken up in 10 mL of ethyl alcohol, 8 mL of 1N sodium hydroxide is added and the resulting mixture is heated under reflux for 2 hours. The solution is cooled, diluted with water and extrated with ethyl acetate. The ethyl acetate extract is washed with brine, dried and filtered. The filtrate is evaporated to yield an oil. This oil is purified by flash chromatography using 2% methyl alcohol in methylene chloride affording 0.71 g of the desired product as a light yellow oil.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hour
  3. temperaturecooled
  4. customquenched with methyl alcohol
  5. customThe volatiles are removed in vacuo
  6. addition8 mL of 1N sodium hydroxide is added
  7. temperaturethe resulting mixture is heated
  8. temperatureunder reflux for 2 hours
  9. temperatureThe solution is cooled
  10. additiondiluted with water
  11. extractionThe ethyl acetate extract
  12. washis washed with brine
  13. customdried
  14. filtrationfiltered
  15. customThe filtrate is evaporated
  16. customto yield an oil
  17. customThis oil is purified by flash chromatography

Sources & evidence

ORD record
ord-101eecf0325d489885997c1f104a9140
Source dataset
uspto-grants-1995_02
Patent number
US05387685

Reaction notes

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