HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → ethyl (1S,5S,6R)-7-acetyl-5-((tert-butoxycarbonyl)amino)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Diisopropyl azodicarboxylate | HCID 5363146 | — |
| Reactant | Ethyl acetate hexane | HCID 21226206 | — |
| Reactant | (3R,4R,5S)-4-Acetylamino-5-tert-butoxycarbonylamino-3-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester | HCID 68364405 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | ethyl (1S,5S,6R)-7-acetyl-5-((tert-butoxycarbonyl)amino)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate | HCID 11594989 | 70% |
Reaction Steps
To a cooled (4° C.) solution of PhMe2P (71 mg; 0.52 mmol) in dichloromethane (1 mL) was added dropwise during 1 min DIAD (104 mg; 0.52 mmol). After additional 5 min of stirring a solution of alcohol 12 (84 mg; 0.24 mmol) and Et3N (7 μL; 0.05 mmol) in dichloromethane (1 mL) was added dropwise. After 10 min the reaction mixture was directly loaded on a silica column. Chromatography [hexane-ethyl acetate (3:1)→(2:1), 6 ml silica] afforded 53 mg (70%) of aziridine 13 as a colourless oil with trace amounts of 14.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08716333B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-533639f3f8eb4d95bb3b4d026dd6b1dd |
| Source note | uspto-grants-2014_05 |