HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → (2s)-(-)-1-(4-Indolyloxy)-3-(spiro[1h-indene-1,4'-piperidin]-1'-yl)-2-propanol ethanedioate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Oxalic Acid | HCID 971 | — |
| Reactant | Spiro[indene-1,4'-piperidine] | HCID 10330052 | — |
| Reactant | (2s)-Glycidyl indol-4-yl ether | HCID 10943254 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (2s)-(-)-1-(4-Indolyloxy)-3-(spiro[1h-indene-1,4'-piperidin]-1'-yl)-2-propanol ethanedioate | HCID 131719706 | — |
Reaction Steps
The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and spiro[1H-indene-1,4'-piperidine]. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 80% overall yield. mp 119°-120°. FDMS m/e=374 (M+ of free base). α[D]589 =-5.51 (c=0.47, methanol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05576321 |
| Source dataset | uspto-grants-1996_11 |
| ORD ID | ord-572e41783b28476e8b617c053c36b59d |
| Source note | uspto-grants-1996_11 |