Potassium Carbonate → tert-butyl (2R,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-[(E)-2-(2-nitrophenyl)ethenyl]morpholine-4-carboxylate

HRID 629696

Reaktionsgleichung

Reaktionsgleichung von HRID 629696
[Si:1]([O:8][CH2:9][C@H:10]1[N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][C@@H:13]([CH:23]=O)[O:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br-].[N+:26]([C:29]1[CH:54]=[CH:53][CH:52]=[CH:51][C:30]=1[CH2:31][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O-:28])=[O:27].C(=O)([O-])[O-].[K+].[K+]>COCCOC>[Si:1]([O:8][CH2:9][C@H:10]1[N:15]([C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[CH2:14][C@@H:13](/[CH:23]=[CH:31]/[C:30]2[CH:51]=[CH:52][CH:53]=[CH:54][C:29]=2[N+:26]([O-:28])=[O:27])[O:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 10885283(2-Nitrobenzyl)triphenylphosphonium bromideHCID 86726303Tert-butyl (2S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-formylmorpholine-4-carboxylate

Produkt 1

HCID 86726304tert-butyl (2R,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-[(E)-2-(2-nitrophenyl)ethenyl]morpholine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

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

Aufarbeitung

  1. filtrationfiltered on celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude product was purified by automated SiO2 flash chromatography system

Quellen und Nachweise

ORD-Eintrag
ord-f29b052624a44ae8a3f46fdc28e7f0ea
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315475B2

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