6-FORMYL-2,3-DIHYDRO-INDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER synthesis
- Product Name:6-FORMYL-2,3-DIHYDRO-INDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
- CAS Number:391668-75-0
- Molecular formula:C14H17NO3
- Molecular Weight:247.29
214614-98-9
391668-75-0
Tert-butyl 6-(hydroxymethyl)indoline-1-carboxylate (163 mg, 0.654 mmol) was used as a raw material and dissolved in 3.2 mL of anhydrous dichloromethane. To this solution was added Dess-Martin periodinane (290 mg, 0.68 mmol) at room temperature. The reaction mixture was stirred at the same temperature for 30 min before the reaction was terminated by adding saturated aqueous NaHCO3 solution. Subsequently, the reaction mixture was extracted with ethyl acetate and the organic phase was washed with brine and dried with anhydrous MgSO4. After filtration to remove the desiccant, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with an eluent ratio of hexane/ethyl acetate (95/5 to 75/25) to afford tert-butyl 6-formylindoline-1-carboxylate as a white powder (140 mg, 86% yield).
214614-98-9
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391668-75-0
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Yield:391668-75-0 86%
Reaction Conditions:
with Dess-Martin periodane in dichloromethane at 20; for 0.5 h;
Steps:
292.1
The above product (163 mg, 0.654 mmol) was dissolved in 3.2 mL of dry dichloromethane, and Dess-Martin periodinane (290 mg, 0.68 mmol) was added to the solution at room temperature. After the reaction mixture was stirred for 30 min at the same temperature, saturated NaHCO3 aqueous solution was added. The mixture was extracted with ethyl acetate, and the extract was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (hexane/ethyl acetate = 95/5 to 75/25) to obtain the title compound as a white powder (140 mg, 86%).
References:
EP2123637,2009,A1 Location in patent:Page/Page column 80