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1,4-Dioxane → (2S,4S)-N-methanesulfonyl-2-tert-butyldimethylsilyloxymethyl-4-diphenylphosphinopyrrolidine

HRID 1638406
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1638406
O1CCOCC1.Cl[P:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Na].[CH3:22][S:23]([N:26]1[CH2:30][C@H:29](OS(C)(=O)=O)[CH2:28][C@H:27]1[CH2:36][O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])(=[O:25])=[O:24]>O1CCCC1>[CH3:22][S:23]([N:26]1[CH2:30][C@@H:29]([P:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:28][C@H:27]1[CH2:36][O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:39])[CH3:40])(=[O:24])=[O:25]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 312751,4-DioxaneHCID 66180ChlorodiphenylphosphineHCID 5360545SodiumHCID 13665135(2S,4R)-N-methanesulfonyl-2-tert-butyldimethylsilyloxymethyl-4-methanesulfonyloxypyrrolidine

Produkt 1

HCID 13665138(2S,4S)-N-methanesulfonyl-2-tert-butyldimethylsilyloxymethyl-4-diphenylphosphinopyrrolidineAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 150 ml of dioxane were added 11.39 g (0.052 mol) of chlorodiphenylphosphine and 2.6 g (0.114 mol) of sodium, and the mixture was refluxed for 4 hours in nitrogen atmosphere. After allowing the mixture to stand for cooling, 50 ml of tetrahydrofuran was added to the reaction mixture, and a solution of 10.45 g (0.027 mol) of (2S,4R)-N-methanesulfonyl-2-tert-butyldimethylsilyloxymethyl-4-methanesulfonyloxypyrrolidine [V] in 100 ml of tetrahydrofuran was added dropwise to the mixture lest any air should enter in the reaction system. The mixture was stirred in nitrogen atmosphere at 0° C. for 2 hours and then at room temperature overnight and then any insoluble matter was removed, for example, by filtration. The filtrate was concentrated until dryness under reduced pressure and the residue was purified by column chromatography on silica gel whereby 7.93 g (yield: 62%) of an oily substance was obtained.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 4 hours in nitrogen atmosphere
  2. temperaturefor cooling
  3. customat room temperature
  4. customovernight
  5. concentrationThe filtrate was concentrated until dryness under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel whereby 7.93 g (yield: 62%) of an oily substance
  7. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-2f511b833e9a47b0bd8bdd3795062de1
Quelldatensatz
uspto-grants-1989_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04879389

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