HCID 13919018, compound → HCID 53802334, compound

HRID 1031776Notes

Reaction equation

HRID 1031776 reaction equation
[CH:1]([N:3]1[CH2:12][CH2:11][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2/[C:4]/1=[CH:13]/[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[O:2]>CO>[CH:1]([N:3]1[CH2:12][CH2:11][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4]1=[CH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[O:2]

Participants

3

Reactant 1

HCID 13919018HCID 13919018, compound

Product 1

HCID 53802334HCID 53802334, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a Schlenk's tube which had previously been dried and purged with argon was weighed and charged 18.8 mg (0.0081 mmol) of [Ru((-)-T-BINAP)SnCl6 ]2NEt3 as a catalyst. Then, 40 ml of degassed anhydrous methanol was added thereto, and the solution was stirred in the presence of hydrogen at room temperature for 2 hours. Separately, a solution of 516 mg (1.82 mmols) of (Z)-N-formyl-1-(4-methoxyphenylmethylene)-3,4,5,6,7,8-hexahydroisoquinoline added to 20 ml of degassed anhydrous methanol was prepared. A fraction of 4.30 ml (molar ratio of substrate/catalyst =1000/1) was taken from the catalyst solution and mixed with a substrate solution. The mixture was transferred into an autoclave and stirred at 75° C. for 47 hours under a hydrogen pressure of 35 kg/cm2. After completion of the stirring, the reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 520 mg of (+)-N-formyl-1-(4-methoxyphenylmethylene)-1,2,3,4,5,6,7,8-octahydroisoquinoline. The yield was 100%.

Workup

  1. customInto a Schlenk's tube which had previously been dried
  2. custompurged with argon
  3. additioncharged 18.8 mg (0.0081 mmol) of [Ru((-)-T-BINAP)SnCl6 ]2NEt3 as a catalyst
  4. additionThen, 40 ml of degassed anhydrous methanol was added
  5. customwas prepared
  6. additionmixed with a substrate solution
  7. stirringstirred at 75° C. for 47 hours under a hydrogen pressure of 35 kg/cm2
  8. concentrationAfter completion of the stirring, the reaction mixture was concentrated under reduced pressure
  9. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-318208c40a544e418429037048cc0a7b
Source dataset
uspto-grants-1990_09
Patent number
US04954644

Reaction notes

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