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Smilagenone → epi-Sarsasapogenin

HRID 2238462
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2238462
C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].[CH3:18][C@H:19]1[CH2:47][O:46][C@@:22]2([O:26][C@H:25]3[CH2:27][C@H:28]4[C@@H:33]5[CH2:34][CH2:35][C@@H:36]6[CH2:42][C:40](=[O:41])[CH2:39][CH2:38][C@:37]6([CH3:43])[C@H:32]5[CH2:31][CH2:30][C@:29]4([CH3:44])[C@H:24]3[C@@H:23]2[CH3:45])[CH2:21][CH2:20]1>C1COCC1>[CH3:18][C@@H:19]1[CH2:47][O:46][C@@:22]2([O:26][C@H:25]3[CH2:27][C@H:28]4[C@@H:33]5[CH2:34][CH2:35][C@@H:36]6[CH2:42][C@H:40]([OH:41])[CH2:39][CH2:38][C@:37]6([CH3:43])[C@H:32]5[CH2:31][CH2:30][C@:29]4([CH3:44])[C@H:24]3[C@@H:23]2[CH3:45])[CH2:21][CH2:20]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 160498SmilagenoneHCID 16684435Lithium tritertbutoxyaluminohydride

Produkt 1

HCID 12304430epi-SarsasapogeninAusbeute 82,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-26.5 °C

Versuchsvorschrift

A solution of lithium tri-tert-butoxyaluminohydride in THF (1M, 41.71 kg) was added (over ca. 2 hours) to a stirred solution of sarsasapogenone (17.38 kg,) in dry THF (ca 70 kg) at −23 to −30° C. under dry nitrogen. The process line was washed with THF and the mixture stirred at −23 to −30° C. for ca. 3 hours. The resulting solution was carefully quenched with aqueous aqueous sodium sulfate solution (5.67 kg in 28.67 kg of water). The inorganic salts were removed by filtration and washed with THF (184 kg). Water (63.18 kg) was added and the bulk of the THF was removed by distillation. Additional water (126.44 kg) was added and the product isolated by filtration. The product was washed with water (2×17.3.8 kg) and acetone (4×13.73 kg). The product was dried at 35-40° C. to afford episarsasapogenin (14.48 kg).

Aufarbeitung

  1. washThe process line was washed with THF
  2. customThe resulting solution was carefully quenched with aqueous aqueous sodium sulfate solution (5.67 kg in 28.67 kg of water)
  3. customThe inorganic salts were removed by filtration
  4. washwashed with THF (184 kg)
  5. additionWater (63.18 kg) was added
  6. customthe bulk of the THF was removed by distillation
  7. additionAdditional water (126.44 kg) was added
  8. customthe product isolated by filtration
  9. washThe product was washed with water (2×17.3.8 kg) and acetone (4×13.73 kg)
  10. customThe product was dried at 35-40° C.

Quellen und Nachweise

ORD-Eintrag
ord-0173458548414fada522a6177c2b6977
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07718792B2

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