HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → trans-Benzyl 3-hydroxy-4-vinylpyrrolidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Heptane | HCID 8900 | — |
| Reactant | HCID 58473021 | HCID 58473021 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | trans-Benzyl 3-hydroxy-4-vinylpyrrolidine-1-carboxylate | HCID 58473027 | 47.9% |
Reaction Steps
The racemic mixture of trans-(±)-benzyl 3-hydroxy-4-vinylpyrrolidine-1-carboxylate (14 g) was resolved by using chiral HPLC (Chiralpak AD-H Heptane:EtOH:MeOH, 8:1:1). The desired enantiomerically enriched (3S,4R)-benzyl 3-hydroxy-4-vinylpyrrolidine-1-carboxylate (6.7 min; 6.3 g, >99.5% ee) and undesired (3R,4S)-benzyl 3-hydroxy-4-vinylpyrrolidine-1-carboxylate (9.3 min; 6.7 g, 99.5% ee) were obtained with 92% recovery.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08546434B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-cc9866b434ba48ab8ccc52b02ca052ef |
| Source note | uspto-grants-2013_10 |