Water → HCID 11077426, compound

HRID 1722817Notes

Reaction equation

HRID 1722817 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].O>C(Cl)Cl.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

5

Reactant 2

HCID 962WaterHCID 11011939HCID 11011939, compound

Product 1

HCID 11077426HCID 11077426, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 6344DichloromethaneSolvent

Procedure

In a glove box, a 500 ml steel autoclave was charged with (E)-2-acetyl-1-(p-methoxybenzylidene)-1,2,3,4,5,6,7,8-octahydroisoquinoline (2.1 g, 7.06 mmol) (prepared according to example 2) 130 ml of methanol, a solution of (+)-CYBIPHEMP (8.2 mg, 0.0142 mmol) and [Ru(TFA)2 (COD)]2 --(H2O) (6.3 mg, 0.007 mmol) in 30 ml of methylene chloride and 5 ml of a solution of 0.0035 mmol of Ru(TFA)2 (BIPHEMP) in methanol. The hydrogenation was run at 100° and 60 bar for 5 h. Work-up as described in example 3 afforded 2.0 g of (S)-2-acetyl-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline, [α]D20 =+45.9° (c=1, methanol), optical purity 86%: e.e. 88.3%.

Workup

  1. customwas run at 100°

Sources & evidence

ORD record
ord-f3d1558a6f1943a7a5dbe3371d3eb75b
Source dataset
uspto-grants-1989_08
Patent number
US04857648

Reaction notes

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