HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 1-Acetyl-3,4-dihydroxy-2-hydroxymethylpyrrolidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | (2R,3R,4R)-3,4-dibenzyloxy-2-benzyloxymethylpyrrolidine | HCID 22842874 | — |
| Reactant | (2R,3R,4R)-1-acetyl-3,4-dibenzyloxy-2-benzyloxy-methylpyrrolidine | HCID 70146873 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 1-Acetyl-3,4-dihydroxy-2-hydroxymethylpyrrolidine | HCID 18426117 | 86% |
| Product | (2R,3R,4R)-1-Acetyl-3,4-dihydroxy-2-hydroxymethylpyrrolidine | HCID 54463964 | — |
Reaction Steps
The title compound was synthesized as described for compound 9 using (2R,3R,4R)-1-acetyl-3,4-dibenzyloxy-2-benzyloxy-methylpyrrolidine (Compound 12) (0.595 g, 1.3 mmol), ethanol (30 ml), methanol (10 ml), 10% Pd/C (0.10 g) and a catalytic amount of 1 M hydrochloric acid. Purification of the product on silica gel (Eluent: Ethyl acetate/methanol (1:1))afford-ed(2R,3R,4R)-1-acetyl-3,4-dihydroxy-2-hydroxymethylpyrrolidine(0.2 g, yield: 86%) as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06451836B1 |
| Source dataset | uspto-grants-2002_09 |
| ORD ID | ord-0ce858f0a06f402bbfc32b6dcdd8959a |
| Source note | uspto-grants-2002_09 |