Methanol → HCID 22161763, compound

HRID 1088809Notes

Reaction equation

HRID 1088809 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][C:16]([CH3:23])([CH3:22])[C:15]2=[O:24])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].[CH3:27]O>>[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][C:16]([CH3:23])([CH3:22])[CH:15]2[O:24][CH3:27])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 22161793HCID 22161793, compound

Product 1

HCID 22161763HCID 22161763, compound

Procedure

To a solution of 8-(t-butyldimethylsilyloxymethyl)-4-oxo-3,3-dimethyl-1-ethyl-1,2,3,4-tetrahydroquinoline (1.60 g) in methanol (20 ml) was added sodium borohydride (0.30 g) and the mixture was stirred for 30 minutes. Methanol was distilled off and the resulting residue was extracted with dichloromethane. After drying the extract over anhydrous magnesium sulfate, the solvent was distilled off. The resulting crude 8-(t-butyldimethylsilyloxymethyl)-4-hydroxy-3,3-dimethyl-1-ethyl-1,2,3,4-tetrahydroquinoline was dissolved in dimethyl formamide (15 ml), followed by addition of sodium hydride (60%, 0.24 g), methyl iodide (0.85 g) was added thereto. The mixture was stirred overnight at room temperature. The reaction mixture was extracted with ethyl acetate-toluene and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (20:1)] to give 8-(t-butyldimethylsilyloxymethyl)- 4-methoxy-3,3-dimethyl-1-ethyl-1,2,3,4-tetrahydroquinoline (1.40 g).

Workup

  1. distillationMethanol was distilled off
  2. extractionthe resulting residue was extracted with dichloromethane
  3. customAfter drying the
  4. extractionextract over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. dissolutionThe resulting crude 8-(t-butyldimethylsilyloxymethyl)-4-hydroxy-3,3-dimethyl-1-ethyl-1,2,3,4-tetrahydroquinoline was dissolved in dimethyl formamide (15 ml)
  7. additionfollowed by addition of sodium hydride (60%, 0.24 g), methyl iodide (0.85 g)
  8. additionwas added
  9. stirringThe mixture was stirred overnight at room temperature
  10. extractionThe reaction mixture was extracted with ethyl acetate-toluene
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationthe solvent was distilled off
  13. customThe resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (20:1)]

Sources & evidence

ORD record
ord-c6c6b46f465442289dc8769356beefc9
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

Loading…