HCID 10946429, compound → HCID 11077426, compound

HRID 2379269Notes

Reaction equation

HRID 2379269 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2/[C:5]/1=[CH:14]/[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:3])[CH3:2]>CO>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C@@H:5]1[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 10946429HCID 10946429, compound

Product 1

HCID 11077426HCID 11077426, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 500 ml autoclave was charged in a glove box with 2 g (6.73 mmol) of (Z)-2-acetyl-1,2,3,4,5,6,7,8-octahydro-1-(p-methoxybenzylidene)isoquinoline (prepared according to any one of Examples 1-4), 170 ml of methanol and 1.3 mg (0.0017 mmol; S/Ru =4000) of Ru(CH3COO)2 (BIPHEMP) as the catalyst. The hydrogenation was carried out at 100° C. and 35 bar for 24 hours. The hydrogenation solution was evaporated and the residue was dissolved in diethyl ether. After separation of the catalyst over silica gel and evaporation of the filtrate, there were obtained 1.98 g of (S)-2-acetyl-1 -(p-methoxybenzyl) -1,2,3,4,5,6,7,8-octahydroisoquinoline of 98.3% e.e., which was recrystallized from diisopropyl ether. [α]D20 =+53° (c=1 in CH3OH); 100% e.e., m.p. 80°-81.5° C.

Workup

  1. customprepared
  2. customwas carried out at 100° C.
  3. customThe hydrogenation solution was evaporated
  4. dissolutionthe residue was dissolved in diethyl ether
  5. customAfter separation of the catalyst
  6. customover silica gel and evaporation of the filtrate

Sources & evidence

ORD record
ord-e0ba025f5e21430599e6be8aea2f70ef
Source dataset
uspto-grants-1994_11
Patent number
US05360908

Reaction notes

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