HCID 10946429, compound → HCID 11077426, compound

HRID 1647352Notes

Reaction equation

HRID 1647352 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 13.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 500 ml autoclave was loaded in a glove box with 15.0 g (50.4 mmol) of (Z)-2-acetyl-1-(p-methoxybenzylidene)-1,2,3,4,5,6,7,8-octahydroisoquinoline, 170 ml of methanol and 3.9 mg (0.0050 mmol) of Ru(CH3COO)2 [(R)-HOBIPHEP] as the catalyst. The hydrogenation was carried out at 100° and 35 bar for 22 hours. The conversion was 98.5%. A 2 g product-containing aliquot of the hydrogenation solution was evaporated and the residue was dissolved in diethyl ether. The ether solution was filtered through a silica gel pad in order to separate the catalyst. Evaporation of the filtrate gave 1.97 g of (S)-2-acetyl-1-(p-methoxybenzyl)-1,2,3.4,5,6,7,8-octahydroisoquinoline as yellowish crystals of 95.9% e.e.

Workup

  1. customwas carried out at 100°
  2. additionA 2 g product-containing aliquot of the hydrogenation solution
  3. customwas evaporated
  4. dissolutionthe residue was dissolved in diethyl ether
  5. filtrationThe ether solution was filtered through a silica gel pad in order
  6. customto separate the catalyst
  7. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-7e73de2a37ab49a7b8786ecac5f4f8f2
Source dataset
uspto-grants-1995_07
Patent number
US05430191

Reaction notes

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