Acetic Acid → (3S,4R)-1-(t-butyldimethylsilyl)3-[(R)-1-hydroxyethyl]-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-one

HRID 64803

Reaktionsgleichung

Reaktionsgleichung von HRID 64803
CCC(C)[BH-](C(C)CC)C(C)CC.[K+].[I-].[K+].[Si:17]([N:24]1[C@H:27]([CH2:28][C:29]([S:34][CH3:35])([S:32][CH3:33])[S:30][CH3:31])[C@@H:26]([C:36](=[O:38])[CH3:37])[C:25]1=[O:39])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].C(O)(=O)C>C(OCC)(=O)C.C(OCC)C>[Si:17]([N:24]1[C@H:27]([CH2:28][C:29]([S:34][CH3:35])([S:32][CH3:33])[S:30][CH3:31])[C@@H:26]([C@H:36]([OH:38])[CH3:37])[C:25]1=[O:39])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 4875Potassium IodideHCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 14127274(3S,4R)-1-(t-butyl dimethylsilyl)-3-(1-oxoethyl)-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-one

Produkt 1

HCID 13104625(3S,4R)-1-(t-butyldimethylsilyl)3-[(R)-1-hydroxyethyl]-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-oneAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

K-Selectride ® (3.64 ml of 0.5M, 1.82 mmol) is added by syringe to a mixture of potassium iodide (126 mg., 0.758 mmol) and (3S,4R)-1-(t-butyl dimethylsilyl)-3-(1-oxoethyl)-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-one (298 mg, 0758 mmol) in freshly distilled ethyl ether (8 ml) at room temperature. The resulting mixture is stirred at room temperature for 2.5 hours, then quenched by the addition of acetic acid (218 mg., 3.64 mmol). The resulting mixture is diluted with ethyl acetate (25 ml) and filtered through celite. Removal of solvents in vacuo gives an oil which is chromatographed on silica gel (ether:petroleum ether) to yield 252 mg of (3S, 4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-[2,2,2-tri(methylthio)ethyl]azetidin-2-one. N.M.R. (R isomer, CDCl3 +D2O) δ4.15(dq,1), δ3.95(ddd,1,J=9.5,2.3), δ3.26(dd,1,J=8,2.3), δ 2.37(m,2), δ2.16(s,9), δ1.37(d,3,J=6,6), δ1.0(s,9), δ0.26(s,6).

Aufarbeitung

  1. filtrationfiltered through celite
  2. customRemoval of solvents in vacuo
  3. customgives an oil which
  4. customis chromatographed on silica gel (ether:petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-8aba69f318e84134a651316dc6c1ce79
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04610820

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