Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 86731273 | HCID 86731273 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 86731274 | HCID 86731274 | 55.6% |
Reaction Steps
To 2-(4-(cyclopropylmethoxy)-3-fluorophenyl)-6,7-dihydro-4H-spiro[1,3-benzoxazole-5,2′-[1,3]dioxolane] (6.00 g) in a mixed solvent of THF (40 mL)-methanol (20 mL)-water (20 mL) was added 6 M hydrochloric acid (17.4 mL), and the mixture was stirred at 70° C. for 1 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. To the organic layer was added sodium tetrahydroborate (657 mg), and the mixture was stirred at room temperature for 20 min. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (2.93 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09133129B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-2d3b1b4361984aa08ed342cc8109e3a1 |
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| Source note | uspto-grants-2015_09 |
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