HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → (2s)-(-)-1-(4-Indolyloxy)-3-(7,8-dimethoxy-2,3,4,5-tetrahydro-1h-3-benzazepin-3-yl)-2-propanol ethanedioate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Oxalic Acid | HCID 971 | — |
| Reactant | (2s)-Glycidyl indol-4-yl ether | HCID 10943254 | — |
| Reactant | 7,8-Dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine | HCID 12923429 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (2s)-(-)-1-(4-Indolyloxy)-3-(7,8-dimethoxy-2,3,4,5-tetrahydro-1h-3-benzazepin-3-yl)-2-propanol ethanedioate | HCID 131719697 | — |
Reaction Steps
The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 48% overall yield. FDMS m/e=396 (M+ of free base). α[D]589 =-9.34 (c=0.47, methanol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05614523 |
| Source dataset | uspto-grants-1997_03 |
| ORD ID | ord-36edb728734748f09595b72196ad8efa |
| Source note | uspto-grants-1997_03 |