HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
2-(Hydroxymethyl)pyrrolidine-3,4-diol → 1,4-Dideoxy-1,4-imino-d-arabinitol
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 2-(Hydroxymethyl)pyrrolidine-3,4-diol | HCID 1335 | — |
| Edukt | D-Tartrate | HCID 5460284 | — |
| Edukt | (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine | HCID 22842874 | — |
| Katalysator | Palladium | HCID 23938 | — |
| Lösungsmittel | Acetic Acid | HCID 176 | — |
| Lösungsmittel | Methanol | HCID 887 | — |
| Produkt | 1,4-Dideoxy-1,4-imino-d-arabinitol | HCID 451991 | — |
| Produkt | D-Tartrate | HCID 5460284 | — |
Reaktionsschritte
A more direct way to synthesise 3,4-dihydroxy-2-hydroxymethylpyrrolidine, D-tartrate is by reduring 2,3,5-Tri-O-benzyl-1,4-dideoxy-1,4-imino-D-arabinitol with Pd/C in glacial acetic acid. The formed, oily (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethyl-pyrrolidine,acetate is dissolved in methanol and added to a solution containing D-tartraric acid at reflux and (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine, D-tartrate is formed and can be isolated by filtration. Ion exchange chromatography is thereby avoided.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US06316489B1 |
| Quelldatensatz | uspto-grants-2001_11 |
| ORD ID | ord-044689dc2fd64923adc958759ad750ed |
| Quellennotiz | uspto-grants-2001_11 |