Ethanol → HCID 10433412, compound

HRID 232238Notes

Reaction equation

HRID 232238 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:16][C:17](=[O:19])[CH3:18])=[C:9]([O:14][CH3:15])[CH:10]=2)/[C:5]/1=[CH:20]/[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][C:30](=[O:32])[CH3:31])[CH:22]=1)(=[O:3])[CH3:2].C(O)C>C(Cl)Cl>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:16][C:17](=[O:19])[CH3:18])=[C:9]([O:14][CH3:15])[CH:10]=2)[C@H:5]1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][C:30](=[O:32])[CH3:31])[CH:22]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 10410926HCID 10410926, compound

Product 1

HCID 10433412HCID 10433412, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
23 °C

Procedure

In a dried Schlenk-tube having its atmosphere displaced with argon, 118.6 mg (0.270 mmol) of (Z)-N-acetyl-7-acetoxy-1-(3-acetoxy-4-methoxyphenylmethylene)-6-methoxy-1,2,3,4-tetrahydroisoquinoline was charged and dissolved in 1.5 ml of methylene chloride. To the solution was further added 7.5 ml of ethanol, followed by degasification by freezing three times. Separately, in a dried Schlenk-tube having its atmosphere displaced with argon, 1.1 mg (6.5×10-4 mmol) of Ru2Cl4 ((R)-(+)-BINAP)2N(C2H5)3 was charged and dissolved in 1.5 ml of methylene chloride which had been previously degassed by freezing three times. To the solution was further added 7.5 ml of ethanol. Both the solutions were transferred to a pressure bottle and subjected to hydrogenation under a hydrogen pressure of 4 atms. at 23° C. for 62 hours while stirring. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography (silica gel: 15 g, eluent: ethyl acetate/hexane=3:1 by volume) to give 104.7 mg (0.237 mmol) of (R)-N-acetyl-7-acetoxy-1-(3-acetoxy-4-methoxyphenylmethyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline (hereinafter referred to as acetylated N-acetylnorreticurine) in a yield of 88%.

Workup

  1. customIn a dried Schlenk-tube having
  2. additionwas charged
  3. customfollowed by degasification
  4. customSeparately, in a dried Schlenk-tube having
  5. additionwas charged
  6. customhad been previously degassed
  7. customAfter completion of the reaction
  8. customthe solvent was removed by distillation under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (silica gel: 15 g, eluent: ethyl acetate/hexane=3:1 by volume)

Sources & evidence

ORD record
ord-cf1ae870279f4563b71fcbf439ef3035
Source dataset
uspto-grants-1989_07
Patent number
US04851537

Reaction notes

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