Citric Acid → HCID 21110582, compound

HRID 1766680Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH3:27])[C:5]([O:11][C:12]2[C:17]([C:18](OCC)=[O:19])=[C:16]([C:23](=[O:25])[CH3:24])[C:15]([OH:26])=[CH:14][CH:13]=2)=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2.[BH4-].[Li+].C(O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.C(OCC)(=O)C.O>[NH2:1][C:2]1[CH:3]=[C:4]([CH3:27])[C:5]([O:11][C:12]2[CH:13]=[CH:14][C:15]([OH:26])=[C:16]([CH:23]([OH:25])[CH3:24])[C:17]=2[CH2:18][OH:19])=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 6-(7-amino-5-methylindan-4-yloxy)-2-acetyl-3-hydroxybenzoate (213 mg) in tetrahydrofuran (15 mL) were added lithium borohydride (390 mg) and ethanol (5 mL). The mixture was stirred at 60° C. for 4 days. To the reaction mixture was added water (10 mL). The mixture was acidified with an 10% aqueous solution of citric acid. To the mixture was added ethyl acetate (20 mL). The reaction mixture was stirred for 1 hour, and extracted with ethyl acetate (×3). The combined organic layers were washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by thin layer chromatography on silica gel (developing solvent: hexane/ethyl acetate=1/1) to give the title compound (66 mg).

Workup

stirringThe reaction mixture was stirred for 1 hour
extractionextracted with ethyl acetate (×3)
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed under reduced pressure
customThe residue was purified by thin layer chromatography on silica gel (developing solvent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-21e633383c124e3dab3a2fa2789fb626
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07230031B2

Reaction notes

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