Acetic Acid → [2-(4-Acetylamino-phenyl)-1,3-dihydroxy-indan-2-yl]-acetic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:26])[CH3:25])=[CH:19][CH:18]=2)[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16])[CH3:2].[BH4-].[Na+].C(O)(=O)C>C(O)C>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1([C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:26])[CH3:25])=[CH:21][CH:22]=2)[CH:14]([OH:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]1[OH:16])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred solution of [2-(4-acetylamino-phenyl)-1,3-dioxo-indan-2-yl]-acetic acid ethyl ester (4.0 g, Reference Example 13) in absolute ethanol (250 mL) was treated portionwise with sodium borohydride (1.7 g). After stirring at room temperature for 4 hours the reaction mixture was treated with glacial acetic acid until pH 7 and then evaporated. The residue was treated with water (100 mL) and the mixture was extracted with ethyl acetate (150 mL). The organic extract was dried over magnesium sulfate and then evaporated. The residue was subjected to chromatography on silica eluting with mixtures of dichloromethane and methanol (from 99.5:5 to 96:4, v/v) to give the title compound (0.7 g) as a solid.
Workup
- customevaporated
- additionThe residue was treated with water (100 mL)
- extractionthe mixture was extracted with ethyl acetate (150 mL)
- extractionThe organic extract
- dry with materialwas dried over magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-4b6f96ec636940caa46e6f39b1ed9080
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07166616B2
Reaction notes
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