Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 3-Pyridinemethanol | HCID 7510 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | (S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide | HCID 66857149 | — |
| Product | HCID 131729711 | HCID 131729711 | — |
Reaction Steps
A mixture of N-[(2S)-5-hydroxy-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (120 mg, 0.470 mmol, Description 3) and 3-pyridinylmethanol (51.3 mg, 0.470 mmol) in dichloromethane (10 ml) was stirred under argon at room temperature. Triphenylphosphine (123 mg, 0.470 mmol) and diisopropyl azodicarboxylate (0.091 ml, 0.470 mmol) were then successively added. The resulting mixture was stirred at room temperature under argon for 16 hours. The reaction mixture was washed with water, dried over sodium sulphate, filtered and evaporated. The desired product was purified by column chromatography on silica eluting with 1 to 99% ethyl acetate in n-pentane and then by SCX column eluting with 1M ammonia in methanol solution to give the title compound as a white solid. The free base solid was dissolved in methanol and treated with ethereal hydrochloride to give the HCl salt (64 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08173820B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-3cf94880f38a495bb4fe5b6c02f72c20 |
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| Source note | uspto-grants-2012_05 |
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