HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → {(S)-6-[(R)-4-(8-Aza-bicyclo[3.2.1]oct-8-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 8-Azabicyclo(3.2.1)octane | HCID 136097 | — |
| Reactant | {(S)-6-[(R)-4-Bromomethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester | HCID 86700813 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | {(S)-6-[(R)-4-(8-Aza-bicyclo[3.2.1]oct-8-ylmethyl)-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester | HCID 90313855 | — |
Reaction Steps
8-Aza-bicyclo[3.2.1]octane (19 mg), KI (27 mg), and K2CO3 (45 mg) are added to a solution of {(S)-6-[(R)-4-bromomethyl-5-trifluoromethyl-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (80 mg) in N,N-dimethylformamide (2 mL) at room temperature. The resulting mixture is stirred at room temperature overnight. Water and brine are added and the mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated to give the crude title compound that is submitted to the next reaction step without further purification. LC (method 6): tR=0.93 min; Mass spectrum (ESI+): m/z=516 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08927531B2 |
| Source dataset | uspto-grants-2015_01 |
| ORD ID | ord-57504d3f0aad4ebdbea8c1b9101c4fc5 |
| Source note | uspto-grants-2015_01 |