HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → tert-Butyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid | HCID 88804 | — |
| Reactant | Diethyl azodicarboxylate | HCID 5462977 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | tert-Butyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate | HCID 11252852 | — |
Reaction Steps
To a solution of (4R)-1-(tert-butoxycarbonyl)-4-hydroxy-L-proline (100 g, 0.443 mol) and PPh3 (227 g, 0.866 mol) in dry THF (1 L) was added dropwise DEAD (151 g, 0.866 mol) at 0° C. under nitrogen. After the addition, the reaction was allowed to warm up to room temperature and stirred overnight. The reaction was concentrated in vacuo and the residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1˜5:1) which gave the title compound Va as a yellow solid (106.5 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08518952B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-6e7ad2a9daa444528db4557935a21a9d |
| Source note | uspto-grants-2013_08 |