Diethyl Ether → (S)-N-((2S,3S)-3,4-bis(tert-butyldimethylsilyloxy)-1-(3-chloro-5-fluorophenyl)butan-2-yl)-2-methylpropane-2-sulfinamide

HRID 1009099

Reaktionsgleichung

Reaktionsgleichung von HRID 1009099
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[CH2:5][Mg]Cl.C(OCC)C.CN(CCN(C)C)C.[Si:25]([O:32][C@H:33]([CH2:42][O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])/[CH:34]=[N:35]/[S@:36]([C:38]([CH3:41])([CH3:40])[CH3:39])=[O:37])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>C1COCC1>[Si:25]([O:32][C@H:33]([CH2:42][O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:45])[CH3:46])[C@@H:34]([NH:35][S@:36]([C:38]([CH3:39])([CH3:40])[CH3:41])=[O:37])[CH2:5][C:4]1[CH:8]=[C:9]([F:11])[CH:10]=[C:2]([Cl:1])[CH:3]=1)([C:28]([CH3:31])([CH3:29])[CH3:30])([CH3:27])[CH3:26]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 44239381(NE,S)-N-[(2S)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]propylidene]-2-methylpropane-2-sulfinamideHCID 178505831HCID 178505831, Verbindung

Produkt 1

HCID 67306214(S)-N-((2S,3S)-3,4-bis(tert-butyldimethylsilyloxy)-1-(3-chloro-5-fluorophenyl)butan-2-yl)-2-methylpropane-2-sulfinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A 500 mL RB flask containing (3-chloro-5-fluorobenzyl)magnesium chloride, 0.25 M in diethyl ether (13040 μl, 3260 μmol) was allowed to stir at −78° C. for 5 minutes. At this time, TMEDA (492 μl, 3260 μmol) was added via a syringe and then THF (10 mL) was added via a syringe and the mixture was allowed to stir for 15 min before the addition of (S,E)-N—((S)-2,3-bis(tert-butyldimethylsilyloxy)propylidene)-2-methylpropane-2-sulfinamide (550.00 mg, 1304 μmol) (14 mL THF) via a syringe. The reaction was allowed to stir for 30 min and then quenched with ammonium chloride (sat, 100 mL). The aq. layer was extracted with EtOAc (3×100 mL). The combined organics were washed with brine and dried with sodium sulfate. The dried solution was filtered and concentrated to give 1.30 g of a crude oil that was purified on a 120 g ISCO column to give the title compound. Rf=0.40 in 20% EtOAc in hexanes.

Aufarbeitung

  1. stirringto stir for 30 min
  2. customquenched with ammonium chloride (sat, 100 mL)
  3. extractionThe aq. layer was extracted with EtOAc (3×100 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationThe dried solution was filtered
  7. concentrationconcentrated
  8. customto give 1.30 g of a crude oil that
  9. customwas purified on a 120 g ISCO column

Quellen und Nachweise

ORD-Eintrag
ord-f1e5cbd0161242a3b14ee65fd4e46afc
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973047B2

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