HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl iodide → 4-Iodo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | (2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester | HCID 2734883 | — |
| Reactant | Diethyl azodicarboxylate | HCID 5462977 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-Iodo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester | HCID 67547214 | — |
Reaction Steps
To a round-bottom flask equipped with a magnetic stir bar and an addition funnel under N2 is added N-Boc-L-trans-4-hydroxy-proline methyl ester, PPh3 and anhydrous THF. The solution is cooled to 0 centigrade, DEAD in THF is added; followed by the addition of MeI. The reaction mixture is allowed to warm to ambient temperature and stirred for about 10 hours. The solvent is removed and the crude product is purified to afford 4-iodo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (31).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07528136B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-289436ba6f3044799cabff8cb406d201 |
| Source note | uspto-grants-2009_05 |