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Dimethyl Sulfoxide → Tert-butyl (2S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-formylmorpholine-4-carboxylate

HRID 629695
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 629695
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Si:11]([O:18][CH2:19][C@H:20]1[N:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][C@@H:23]([CH2:33][OH:34])[O:22][CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl.O>[Si:11]([O:18][CH2:19][C@H:20]1[N:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][C@@H:23]([CH:33]=[O:34])[O:22][CH2:21]1)([C:14]([CH3:17])([CH3:15])[CH3:16])([CH3:13])[CH3:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86726301Tert-butyl (2S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-(hydroxymethyl)morpholine-4-carboxylate

Produkt 1

HCID 86726303Tert-butyl (2S,5S)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-formylmorpholine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel4×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a stirred solution of oxalyl chloride (2 eq) in DCM (0.3 M) at −78° C. was added a solution of DMSO (5 eq) in DCM (0.5M). The reaction mixture was stirred at −78° C. for 30 min. A solution of tert-butyl (2S,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-(hydroxymethyl)morpholine-4-carboxylate (1 eq) in CH2Cl2 (0.2M) was added dropwise and stirred at −40° C. for 1.5 hours. It was then cooled to −78° C. and triethylamine (7 eq) was added and the reaction mixture was stirred at 0° C. for 1 h. Water was added and the reaction mixture was warmed to rt for 30 min. The mixture was diluted with CH2Cl2, the organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated. The crude product was used as such for the next step.

Aufarbeitung

  1. stirringstirred at −40° C. for 1.5 hours
  2. temperatureIt was then cooled to −78° C.
  3. stirringthe reaction mixture was stirred at 0° C. for 1 h
  4. temperaturethe reaction mixture was warmed to rt for 30 min
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4eb63425462545c59f4669ca39e92ca9
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09315475B2

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