Methanol → HCID 11077426, compound

HRID 1722816Notes

Reaction equation

HRID 1722816 reaction equation
O=O.[C:3]([N:6]1[CH2:15][CH2:14][C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2/[C:7]/1=[CH:16]\[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:5])[CH3:4].CO.C(Cl)Cl>C(OCC)C>[C:3]([N:6]1[CH2:15][CH2:14][C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[C@@H:7]1[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 977OxygenHCID 6344DichloromethaneHCID 11011939HCID 11011939, compound

Product 1

HCID 11077426HCID 11077426, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a glove box (<1 ppm oxygen), a 500 ml steel autoclave was charged with 2-acetyl-1-(p-methoxybenzyl)-2,3,4,6,7,8-hexahydroisoquinoline (2.43 g, 8.17 mmol) (prepared according to example 2) 40 ml of methanol, 28 ml of methylene chloride and 100 ml of a methanol solution containing 0.082 mmol of Ru(TFA)2 (BIPHEMP) as catalyst. The hydrogenation was carried out at 100° and 60 bar for 20 h. The solution was concentrated to give an oil, which was dissolved in 300 ml of diethyl ether. To removed the catalyst the ether solution was passed through a short pad of silica gel. Concentration of the filters afforded 2.4 g of (S)-2-acetyl-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline as a colorless oil; e.e. 94.3%.

Workup

  1. customwas carried out at 100°
  2. concentrationThe solution was concentrated
  3. customto give an oil, which
  4. customTo removed the catalyst the ether solution

Sources & evidence

ORD record
ord-2ba70a70e0e84374a185b94a1227268a
Source dataset
uspto-grants-1989_08
Patent number
US04857648

Reaction notes

Loading…