Tetrahydrofuran → HCID 22467381, compound
Reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:7]([CH:11]=1)[C:8]([OH:10])=[O:9])#N.CCCCCC.[H-].C([Al+]CC(C)C)C(C)C.[O:34]1CCCC1>>[CH:13]1([NH:12][C:6]2[CH:5]=[CH:4][C:3]([CH:1]=[O:34])=[CH:11][C:7]=2[C:8]([OH:10])=[O:9])[CH2:17][CH2:16][CH2:15][CH2:14]1Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 5-cyano-2-(cyclopentylamino)benzoic acid (40.0 mg) in anhydrous tetrahydrofuran (2 mL) was added 1.5 M diisobutylaluminium hydride hexane solution (0.34 mL) under dry ice-acetone cooling, and the mixture was stirred for an hour at −78° C. and then for 4 hours at ambient temperature. The reaction was quenched by addition of methanol and an aqueous saturated ammonium chloride solution. After stirring at ambient temperature for a half hour, the mixture was partitioned with 5% sulfuric acid and chloroform. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a preparative silica gel chromatography with 10% methanol in chloroform to give 2-(cyclopentylamino)-5-formylbenzoic acid (25.0 mg) as pale orange powders.
Workup
- customThe reaction was quenched by addition of methanol
- stirringAfter stirring at ambient temperature for a half hour
- customthe mixture was partitioned with 5% sulfuric acid and chloroform
- washThe separated organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
- customThe residue was purified by a preparative silica gel chromatography with 10% methanol in chloroform
Sources & evidence
- ORD record
- ord-364a82645be547dbb363c79b078b90db
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06384080B1
Reaction notes
Loading…