HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Bromoethyl isocyanate → (3aSR,10RS)-2-(2-Bromo-ethyl)-6-ethoxy-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Bromoethyl isocyanate | HCID 4255957 | — |
| Reactant | (1RS,3SR)-1-(3-hydroxy-phenyl)-6-ethoxy-3-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid methyl ester | HCID 68886227 | — |
| Solvent | Methyl Ethyl Ketone | HCID 6569 | — |
| Product | (3aSR,10RS)-2-(2-Bromo-ethyl)-6-ethoxy-10-(3-hydroxy-phenyl)-3a-methyl-3a,4,9,10-tetrahydro-2,9,10a-triaza-cyclopenta[b]fluorene-1,3-dione | HCID 68937590 | 40% |
Reaction Steps
To a solution of 500 mg (1.31 mmol) (1RS,3SR)-6-Ethoxy-1-(3-hydroxy-phenyl)-3-methyl-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid methyl ester in 25 ml 2-butanon are added 120 μl (1.31 mmol) bromoethyl isocyanate. The mixture is heated to reflux for 24 h. The solvent is removed under reduced pressure. The crude product is purified by column chromatography (silica gel; toluene, ethyl acetate 6:1). 260 mg (40%) of the title compound are obtained as a colorless solid. m.p.: 250-252° C., MS: m/z (MH+)=498.1/500.0
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08530493B2 |
| Source dataset | uspto-grants-2013_09 |
| ORD ID | ord-90fd3c185f8b4a22bad918afbe59d1b6 |
| Source note | uspto-grants-2013_09 |