Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | HCID 66897908 | HCID 66897908 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 66898186 | HCID 66898186 | 62.4% |
Reaction Steps
To a mixture of ethyl {2-[7-(2-methoxy-1-methylethoxy)-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (660 mg), tetrahydrofuran (30 mL) and methanol (5 mL) was added lithium borohydride (130 mg) at 0° C. The whole was stirred at room temperature for 5 h. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:1 to 1:0, volume ratio) to give pale yellow crystals. The crystals were recrystallized from ethyl acetate-hexane to give the title compound (380 mg, 62%) as pale yellow prisms. MS 506 (MH+). mp 138-139° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08673942B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-b69f8d02267a49e48b3cee8d33f1166b |
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| Source note | uspto-grants-2014_03 |
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