HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → (2s)-(-)-1-(4-Indolyloxy)-3-(4-hydroxy-4-(3-trifluoromethyl-4-chlorophenyl)piperidin-1-yl)-2-propanol ethanedioate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Oxalic Acid | HCID 971 | — |
| Reactant | 4-(4-Chloro-3-(trifluoromethyl)phenyl)piperidin-4-ol | HCID 89107 | — |
| Reactant | (2s)-Glycidyl indol-4-yl ether | HCID 10943254 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (2s)-(-)-1-(4-Indolyloxy)-3-(4-hydroxy-4-(3-trifluoromethyl-4-chlorophenyl)piperidin-1-yl)-2-propanol ethanedioate | HCID 131719693 | — |
Reaction Steps
The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 4-hydroxy-4-(3-trifluoromethyl-4-chlorophenyl)piperidine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 85% overall yield. FDMS m/e=469 (M+ of free base). α[D]589 =-11.53 (c=0.54, methanol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05789402 |
| Source dataset | uspto-grants-1998_08 |
| ORD ID | ord-2fada90b79954aea9cc2b07d72d85ec4 |
| Source note | uspto-grants-1998_08 |