HCID 11011939, compound → HCID 11077426, compound

HRID 1722818Notes

Reaction equation

HRID 1722818 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]>C(Cl)Cl>[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 11011939HCID 11011939, compound

Product 1

HCID 11077426HCID 11077426, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (E)-2-acetyl-1,2,3,4,5,6,7,8-octahydro-1-(p-methoxybenzylidene)isoquinoline (2.1 g) in methylene chloride (120 ml) was refluxed under argon for 2 h. The reaction mixture was concentrated to a final volume of 30 ml at 25°/20 mbar and transferred into a 500 ml autoclave, followed by 90 ml of methanol and 50 ml of a methanol solution containing 0.035 mmol of Ru(TFA)2 (BIPHEMP). Hydrogenation at 100°, 60 bar and work-up as described in example 3 afforded 2.08 of (S)-2-acetyl-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline; [α]D20 =+51.2° (c-1, methanol), optical purity 97.3% e.g., 97.6%.

Workup

  1. concentrationThe reaction mixture was concentrated to a final volume of 30 ml at 25°/20 mbar
  2. customat 100°

Sources & evidence

ORD record
ord-e7d4d4a813ba450a9c62c666128ba473
Source dataset
uspto-grants-1989_08
Patent number
US04857648

Reaction notes

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