HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → (2S)-(-)-1-(4-indolyloxy)-3-(spiro[indane-1,4'-piperidin]-1'-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 | 2,3-Dihydrospiro(indene-1,4'-piperidine) | HCID 15637616 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (2S)-(-)-1-(4-indolyloxy)-3-(spiro[indane-1,4'-piperidin]-1'-yl)-2-propanol ethanedioate | HCID 131719705 | — |
Reaction Steps
The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and spiro[indane-1,4′-piperidine]. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 76% overall yield. mp 110-112°. FDMS m/e=376 (M+ of free base). α[D]589=−11.60 (c=0.46 methanol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06172073B2 |
| Source dataset | uspto-grants-2001_01 |
| ORD ID | ord-2725641b9e65462891b4757fb19d6af4 |
| Source note | uspto-grants-2001_01 |