HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Chloride → (1S,2S)-2-{4-[(R)-5-Cyano-4-(4-hydroxy-2,6-dimethyl-phenyl)-indan-1-yloxy]-phenyl}cyclopropanecarboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | HCID 86703878 | HCID 86703878 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (1S,2S)-2-{4-[(R)-5-Cyano-4-(4-hydroxy-2,6-dimethyl-phenyl)-indan-1-yloxy]-phenyl}cyclopropanecarboxylic acid ethyl ester | HCID 86703880 | 77.1% |
Reaction Steps
(1S,2S)-2-(4-{(R)-4-[4-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-phenyl]-5-cyano-indan-1-yloxy}-phenyl)-cyclopropanecarboxylic acid ethyl ester (500 mg, 0.86 mmol) is dissolved in 10 mL of tetrahydrofuran, a 1 M aqueous solution of tetrabutylammonium fluoride (2 mL, 2.00 mmol) is added and the reaction mixture is stirred at room temperature for 3 h. 2 mL of an ammonium chloride saturated aqueous solution is added and the reaction mixture is concentrated under vacuum. The crude product obtained is purified by flash chromatography (cyclohexane/ethyl acetate 100/01→50/50) to give the title compound (Yield: 310 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08633182B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-9a60e37492cb4c548df1f7c716fd790f |
| Source note | uspto-grants-2014_01 |