Methanol → HCID 53981621, compound

HRID 1590846Notes

Reaction equation

HRID 1590846 reaction equation
[C:1]([N:4]1[CH2:13][C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[C:16]([O:22]C)[CH:15]=2)[C:11]2[C:6](=[C:7]([O:26]C)[C:8]([O:24]C)=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].B(Br)(Br)Br.ClCCl.CO>ClCCl>[C:1]([N:4]1[CH2:13][C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([OH:22])[CH:15]=2)[C:11]2[C:6](=[C:7]([OH:26])[C:8]([OH:24])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 22277759Boron tribromide dichloromethaneHCID 54226046(R)-(-)-N-acetyl-7,8-dimethoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 53981621HCID 53981621, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(i)1.78 g of (R)-(-)-N-acetyl-7,8-dimethoxy-4-(3,4-dimethoxyphenyl)-1,2,3,4-tetrahydroisoquinoline was dissolved in 9 ml of dichloromethane; after adding 24 ml of 1M boron tribromide-dichloromethane solution at -30 ° C., the mixture was reacted at room temperature for 90 minutes. Then 4.4 ml of methanol was added at -30° C. The reaction solution was concentrated and subjected twice to azeotropic distillation with methanol. To the residue was added 17.8 ml of 0.1N hydrochloric acid. The crystals which separated out were collected by filtration, affording 1.46 g of (R)-(-)-N-acetyl-7,8-dihydroxy-4-(3,4-dihyroxyphenyl)-1,2,3,4-tetrahydroisoquinoline.1/4 hydrate, m.p. above 230° C. (decomposition): [α]D20 =-85° (C=1, CH3OH)

Workup

  1. customthe mixture was reacted at room temperature for 90 minutes
  2. concentrationThe reaction solution was concentrated
  3. distillationsubjected twice to azeotropic distillation with methanol
  4. additionTo the residue was added 17.8 ml of 0.1N hydrochloric acid
  5. customThe crystals which separated out
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-0cbf35d8295e4687a514a5b1769d541a
Source dataset
uspto-grants-1993_04
Patent number
US05204468

Reaction notes

Loading…