HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 58503489, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (4-Methoxyphenyl)boronic acid | HCID 201262 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | 8-Benzyl-3-(trifluoromethylsulfonyloxy)-8-azabicyclo[3.2.1]oct-3-ene | HCID 49835910 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 58503489 | HCID 58503489 | — |
Reaction Steps
4-Methoxyphenyl boronic acid (0.50 g), lithium chloride (0.26 g), Pd(PPh3)4 (0.17 g), and finally 2 M aqueous Na2CO3 solution (3.2 mL) are added in turn to a flask charged with a stir bar, trifluoromethanesulfonic acid 8-benzyl-8-aza-bicyclo[3.2.1]oct-2-en-3-yl ester (1.0 g), water (5 mL), and 1,2-dimethoxyethane (25 mL) under argon atmosphere. The resulting mixture is stirred at reflux temperature for 5 h. After cooling to ambient temperature, brine is added and the mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and the solvent is removed under reduced pressure. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:0→1:1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08829027B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-69cee5192e414aff8ce54bb55ce00555 |
| Source note | uspto-grants-2014_09 |