Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | HCID 70562050 | HCID 70562050 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 70564472 | HCID 70564472 | — |
Reaction Steps
To a solution of methyl 2-(4-chlorophenyl)-2-(6-fluoro-4-(methylsulfonamido)-1H-indol-1-yl)butanoate (0.5 g, 1.14 mmol) in THF (5 mL) was added dropwise lithium aluminum hydride solution (1.4 mL, 1 M in THF) at −78° C. The reaction mixture was stirred for 0.5 hours at −78° C. TLC and LCMS monitored the reaction was over, then 3M HCl solution was added carefully into the reaction to adjust pH=2˜3 in ice bath. The organic layer was separated and the aqueous layer was extracted with EA. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate. The resulting mixture was filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography (PE: EA=2:1) to afford the title compound. LC/MS m/z=411.1 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09403807B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-fe223d2169db4722a7a35f69023633e4 |
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| Source note | uspto-grants-2016_08 |
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