HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → 1-Benzylpyrrolidine-3-carbaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Sulfoxonium, trimethyl-, iodide (1:1) | HCID 74498 | — |
| Reactant | Phenolate Sodium | HCID 4445035 | — |
| Reactant | (1-Benzylpyrrolidin-3-yl)methanol | HCID 5176654 | — |
| Reactant | Dimethylsulfoxonium methylide | HCID 6396768 | — |
| Reactant | HCID 178418287 | HCID 178418287 | — |
| Product | 1-Benzylpyrrolidine-3-carbaldehyde | HCID 4589478 | — |
| Product | 1-Phenylmethyl-alpha-phenoxymethyl-2-pyrrolidinemethanol | HCID 20039787 | — |
Reaction Steps
1-Phenylmethyl-3-formylpyrrolidine is prepared from 1-phenylmethyl-3-hydroxymethyl pyrrolidine (source: method of U.S. Pat. No. 3,318,908) by reacting it with pyridinium chlorochromate and converted to the corresponding 3-epoxide using dimethyloxosulfonium methylide obtained by mixing trimethylsulfoxonium iodide and sodium hydride in aprotic solvent. The epoxide is reacted with sodium phenoxide and the reaction mixture is acidified to give 1-phenylmethyl-α-phenoxymethyl-2-pyrrolidinemethanol which is hydrogenated over palladium on carbon to give the free base of the title compound. The free base is converted to the hydrochloride salt as in Example 38.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04835164 |
| Source dataset | uspto-grants-1989_05 |
| ORD ID | ord-00ddace851d442d699fafbac4cf28083 |
| Source note | uspto-grants-1989_05 |