Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | HCID 68381853 | HCID 68381853 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67119152 | HCID 67119152 | 37% |
Reaction Steps
Ethyl (2-{7-(1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (330 mg) was dissolved in a mixture of tetrahydrofuran (15 mL) and methanol (3 mL). Lithium borohydride (30 mg) was added to the mixture at room temperature and the mixture was stirred at room temperature for 30 min. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90 to 80/20, volume ratio) to give the title compound (112 mg, 37%) as a pale yellow amorphous solid. MS 475 (MH+).
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-db629ab1a0e74b2ca082d47119e47cfd |
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| Source note | uspto-grants-2014_03 |
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