Water → 4-Acetoxy-6-s-butyl-8-hydroxymethyl-2,3-dimethylquinoline
Reaction equation
[C:1]([O:4][C:5]1[C:14]2[C:9](=[C:10]([CH:19]=[O:20])[CH:11]=[C:12]([CH:15]([CH2:17][CH3:18])[CH3:16])[CH:13]=2)[N:8]=[C:7]([CH3:21])[C:6]=1[CH3:22])(=[O:3])[CH3:2].[BH4-].[Na+].O>CO>[C:1]([O:4][C:5]1[C:14]2[C:9](=[C:10]([CH2:19][OH:20])[CH:11]=[C:12]([CH:15]([CH2:17][CH3:18])[CH3:16])[CH:13]=2)[N:8]=[C:7]([CH3:21])[C:6]=1[CH3:22])(=[O:3])[CH3:2]Participants
Procedure
210 Milligrams of 4-acetoxy-6-s-butyl-8-formyl-2,3-dimethylquinoline obtained in Example 33 was dissolved in 4 ml of methanol, to which 7 mg of sodium borohydride dissolved in 4 ml of methanol was added dropwise and the mixture was stirred at room temperature for 1 minute. After the addition of 20 ml of water, the reaction mixture was extracted with ethyl acetate. The resultant organic layer was washed with a saturated brine and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the resultant crude product was purified by column chromatography on silica gel (WAKOGEL® C-200) eluting with n-hexane/ethyl acetate (10:1) to obtain 186 mg of 4-acetoxy-6-s-butyl-8-hydroxymethyl-2,3-dimethylquinoline (yield 84%). Its NMR spectral data are shown in the following Table 2.
Workup
- additionwas added dropwise
- extractionthe reaction mixture was extracted with ethyl acetate
- washThe resultant organic layer was washed with a saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customAfter the solvent was evaporated under reduced pressure
- customthe resultant crude product was purified by column chromatography on silica gel (WAKOGEL® C-200)
- washeluting with n-hexane/ethyl acetate (10:1)
Sources & evidence
- ORD record
- ord-fa5d204045c741d8b288341c120e4806
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07067668B2
Reaction notes
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