Boron tribromide → HCID 21480575, compound

HRID 1490162Notes

Reaction equation

HRID 1490162 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:12][CH:11]2[CH:6]([CH2:7][CH2:8][CH:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)[CH2:10]2)[NH:5][C:4]1=[O:22].B(Br)(Br)Br>ClCCl>[OH:1][CH2:2][CH:3]1[CH2:12][CH:11]2[CH:6]([CH2:7][CH2:8][CH:9]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=3)[CH2:10]2)[NH:5][C:4]1=[O:22]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21480573HCID 21480573, compound

Product 1

HCID 21480575HCID 21480575, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

3,4,4a,5,6,7,8,8a,-Octahydro-3-hydroxymethyl-6-((4-methoxyphenyl)methyl)-quinolin-2[1H]-one (0.26 g) (prepared according to Example 7) was dissolved in dichloromethane and cooled to ice temperature. 1M Boron tribromide in dichloromethane (4.3 ml) was added and the mixture was left 2 hours after which a further 75 ml of dichloromethane was added. After a further 1 hour the reaction mixture was quenched by addition of water (2 ml) and evaporated under reduced pressure. The residue was dissolved in methanol (100 ml) containing conc. HCl (1 ml) and the methanol was evaporated under reduced pressure; the process being repeated three time. The residue was basified with saturated sodium bicarbonate solutions and was extracted into chloform. The chloroform layer was dried (MgSO4) and evaporated. The residue was recrystallised from isopropanol/diisopropyl ether to give the title compound (0.035 g) mp 126°-128° C.

Workup

  1. temperaturecooled to ice temperature
  2. additionwas added
  3. customAfter a further 1 hour the reaction mixture was quenched by addition of water (2 ml)
  4. customevaporated under reduced pressure
  5. dissolutionThe residue was dissolved in methanol (100 ml)
  6. additioncontaining conc. HCl (1 ml)
  7. customthe methanol was evaporated under reduced pressure
  8. extractionwas extracted into chloform
  9. dry with materialThe chloroform layer was dried (MgSO4)
  10. customevaporated
  11. customThe residue was recrystallised from isopropanol/diisopropyl ether

Sources & evidence

ORD record
ord-13b22f2dc343402bb37be3adf441f645
Source dataset
uspto-grants-1997_10
Patent number
US05681839

Reaction notes

Loading…