Lithium tri-s-butylborohydride → (R)-2-methyl-propane-2-sulfinic acid [(S)-1-(5-methanesulfonyl-furan-2-yl)-propyl]amide

HRID 1361168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361168
[CH3:1][S:2]([C:5]1[O:9][C:8](/[C:10](=[N:13]/[S@@:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])/[CH2:11][CH3:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>C1COCC1>[CH3:1][S:2]([C:5]1[O:9][C:8]([C@@H:10]([NH:13][S@@:14]([C:16]([CH3:17])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH3:12])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Komponenten

4

Edukt 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 59278140(NE,R)-2-methyl-N-[1-(5-methylsulfonylfuran-2-yl)propylidene]propane-2-sulfinamide

Produkt 1

HCID 59278508(R)-2-methyl-propane-2-sulfinic acid [(S)-1-(5-methanesulfonyl-furan-2-yl)-propyl]amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a chilled (−78° C.) solution of (R)-2-methyl-propane-2-sulfinic acid[1-(5-methanesulfonyl-furan-2-yl)-prop-(E)-ylidene]-amide (0.360 g, 1.18 mmol) in THF (15 mL) was added a 1 M solution of L-Selectride (2.4 mL, 2.4 mmol) in THF in several portions. After stirring for 2 hours, the mixture was quenched with saturated aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in hexanes to afford (R)-2-methyl-propane-2-sulfinic acid [(S)-1-(5-methanesulfonyl-furan-2-yl)-propyl]-amide.

Aufarbeitung

  1. customthe mixture was quenched with saturated aqueous ammonium chloride (100 mL)
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined organic layers were washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by silica gel chromatography
  8. washeluting with a gradient of 0-100% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-953ece4043eb433192b7dfa3fccc2fe5
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879873B2

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