HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Azide → cis-4-Azido-2-benzhydryl-tetrahydropyran
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | methanesulfonic acid Trans-2-benzhydryl-tetrahydropyran-4-yl ester | HCID 86605343 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | cis-4-Azido-2-benzhydryl-tetrahydropyran | HCID 86605345 | 82.7% |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
Into a solution of trans-2-diphenylmethylpyran-4-yl methanesulfonate 4a (0.33 g, 0.95 mmol) in dry DMF (40 ml) was added sodium azide (0.18 g, 2.85 mmol). The mixture was heated to 100° C. and stirred for 4 hr. The mixture was diluted with ethyl ether, washed with 2M aqueous NaHCO3 and brine, and then dried over anhydrous Na2SO4. Removal of the solvent and purification by flash chromatography (Hexane/Ethyl Acetate 9:1) afforded compound 5a (0.23 g, 82.7% yield) as a liquid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08519159B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-040c8d8e7b9b4fc59f915424e98ccb8e |
| Source note | uspto-grants-2013_08 |