HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → [7-(2-Benzyloxycarbonylamino-ethyl)-1-(3-chloro-benzyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-carbamic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Potassium benzyl N-[2-(trifluoroboranuidyl)ethyl]carbamate | HCID 49761741 | — |
| Reactant | 8-(3-Chlorobenzyl)-7-(ethoxycarbonylamino)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate | HCID 57476723 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene water | HCID 22272177 | — |
| Product | [7-(2-Benzyloxycarbonylamino-ethyl)-1-(3-chloro-benzyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-carbamic acid ethyl ester | HCID 57476722 | 75.6% |
Reaction Steps
A mixture of potassium (2-(benzyloxycarbonylamino)ethyl)trifluoroborate (1,130 g, 3.96 mmol), cesium carbonate (2.58 g, 7.93 mmol), 8-(3-chlorobenzyl)-7-(ethoxycarbonylamino)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (1.3 g, 2.64 mmol), Pd(OAc)2 (0.030 g, 0.132 mmol) and 2-dicyclohexyphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl (0.130 g, 0.264 mmol) under N2 in toluene/water 3:1 (15 ml) was heated to refluxed for 13 h. The reaction was filtered, the solvent evaporated and the residue purified by chromatography to afford 1.04 g of product as colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09096619B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-3367daee929544e3930e5fee4a099335 |
| Source note | uspto-grants-2015_08 |