Hydrogen Peroxide → HCID 22161767, compound

HRID 1088807Notes

Reaction equation

HRID 1088807 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]([CH2:20][CH3:21])[CH2:17][CH2:16][C:15]2=[CH2:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH2:23].[OH-].[Na+].OO>O1CCCC1>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]([CH2:20][CH3:21])[CH2:17][CH2:16][CH:15]2[CH2:22][OH:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 22161779HCID 22161779, compound

Product 1

HCID 22161767HCID 22161767, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 8-(t-butyldimethylsilyloxymethyl)-4-methylene-1-ethyl-1,2,3,4-tetrahydroquinoline (2.04 g) in tetrahydrofuran (50 ml), 10M solution (3.2 m) of borane-dimethylsulfide complex in tetrahydrofuran was added dropwise with stirring under ice-cooling. After stirring the mixture for 2 hours at room temperature, water was added to the reaction mixture, and furthermore 3N aqueous solution of sodium hydroxide (10 ml) and 30% hydrogen peroxide (10 ml) were added thereto. After stirring for 2 hours at room temperature, the reaction mixture was subjected to salting-out and extracted with dichloromethane. After the extract was dried, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (3:1)]to give 8-(t-butyldimethylsilyloxymethyl)-4-hydroxymethyl-1-ethyl-1,2,3,4-tetrahydroquinoline (1.98 g).

Workup

  1. temperaturecooling
  2. stirringAfter stirring the mixture for 2 hours at room temperature
  3. additionwere added
  4. stirringAfter stirring for 2 hours at room temperature
  5. extractionextracted with dichloromethane
  6. customAfter the extract was dried
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography [eluent

Sources & evidence

ORD record
ord-91f755737e1c430b8693691ef91ef3ab
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

Loading…