Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | (2,6-Dimethylpyridin-3-yl)methanol | HCID 2784752 | — |
| Reactant | Diisopropyl azodicarboxylate | HCID 5363146 | — |
| Reactant | (S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide | HCID 66857149 | — |
| Product | HCID 131729712 | HCID 131729712 | — |
Reaction Steps
A mixture of N-[(2S)-5-hydroxy-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (149 mg, 0.583 mmol, Description 3) and (2,6-dimethyl-3-pyridinyl)methanol (80 mg, 0.583 mmol) in dichloromethane (10 ml) was stirred under argon at room temperature. Triphenylphosphine (153 mg, 0.583 mmol) and DIAD (0.113 ml, 0.583 mmol) were then successively added. The resulting mixture was stirred at room temperature under argon for 16 hours. Then the reaction mixture was washed with water, dried over sodium sulphate, filtered and evaporated. The desired product was isolated by MDAP, concentrated to a small volume, and partitioned between dichloromethane and aqueous sodium hydrogen carbonate solution. The organic phase was dried over sodium sulphate, filtered and evaporated in vacuo to afford the desired compound as a free base. This was treated with ethereal hydrochloride/methanol to give the title compound as a white solid (92 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-65f03937783b4d7bbb37e686908b55b6 |
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| Source note | uspto-grants-2012_05 |
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