HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Potassium Carbonate → tert-butyl (2R,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-[(E)-2-(2-nitrophenyl)ethenyl]morpholine-4-carboxylate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Edukt | (2-Nitrobenzyl)triphenylphosphonium bromide | HCID 10885283 | — |
| Edukt | Tert-butyl (2S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-formylmorpholine-4-carboxylate | HCID 86726303 | — |
| Lösungsmittel | 1,2-Dimethoxyethane | HCID 8071 | — |
| Produkt | tert-butyl (2R,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-[(E)-2-(2-nitrophenyl)ethenyl]morpholine-4-carboxylate | HCID 86726304 | — |
Reaktionsschritte
To tert-butyl (2S,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-formylmorpholine-4-carboxylate (1 eq.) in DME (0.2 M) at rt were added (2-nitrobenzyl)(triphenyl)phosphonium bromide (1.1 eq.), potassium carbonate (2 eq.) and 18-C-6 (0.1 eq.). The reaction mixture was stirred at rt for 12 hrs, filtered on celite and the filtrate was concentrated under reduced pressure. The crude product was purified by automated SiO2 flash chromatography system using solvent gradient of 10% to 60% EtOAc/Hex to afford the desired compound
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09315475B2 |
| Quelldatensatz | uspto-grants-2016_04 |
| ORD ID | ord-f29b052624a44ae8a3f46fdc28e7f0ea |
| Quellennotiz | uspto-grants-2016_04 |