HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-Methoxy 3-(1,2,3,6-tetrahydro-4-pyridinyl)1H indole → (2S)-(+)-3-[4-(5-methoxy-3-indolyl)-1,2,3,6-tetrahydropyridin-1-yl]-1-(4-indolyloxy)-2-propanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-Methoxy 3-(1,2,3,6-tetrahydro-4-pyridinyl)1H indole | HCID 108029 | — |
| Reactant | (2s)-Glycidyl indol-4-yl ether | HCID 10943254 | — |
| Solvent | Dimethyl sulfoxide methanol | HCID 22036561 | — |
| Product | (2S)-(+)-3-[4-(5-methoxy-3-indolyl)-1,2,3,6-tetrahydropyridin-1-yl]-1-(4-indolyloxy)-2-propanol | HCID 57079702 | — |
Reaction Steps
The title compound was prepared in a fashion similar to that described in Example 193 from 5-methoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (0.70 g, 3.1 mmol) and (S)-(+)-4-(oxiranylmethoxy)-1H-indole (0.58 g, 3.1 mmol). The product was isolated as a yellow foam. Yield 245 mg (19%). mp 105°-110° C. FDMS m/e=417 (M+ of free base). α[D]589 =+7.52 (c=1.01, methanol/dimethylsulfoxide).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05614523 |
| Source dataset | uspto-grants-1997_03 |
| ORD ID | ord-166cb8f7261b485b8ac8b4ae9e758adb |
| Source note | uspto-grants-1997_03 |