Water → 5beta-Cholane-3alpha,12alpha,24-triol

HRID 1464250

Reaktionsgleichung

Reaktionsgleichung von HRID 1464250
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:29])[C@@H:14]([OH:28])[CH2:15][C@@H:16]3[C@@:21]4([CH3:27])[CH2:22][CH2:23][C@@H:24]([OH:26])[CH2:25][C@H:20]4[CH2:19][CH2:18][C@H:17]3[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][C:5](OC)=[O:6].O>C1COCC1>[OH:26][C@@H:24]1[CH2:23][CH2:22][C@@:21]2([CH3:27])[C@H:20]([CH2:19][CH2:18][C@@H:17]3[C@@H:16]2[CH2:15][C@H:14]([OH:28])[C@@:13]2([CH3:29])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C@H:2]([CH3:1])[CH2:3][CH2:4][CH2:5][OH:6])[CH2:25]1

Komponenten

4

Edukt 2

HCID 962WaterHCID 229346Methyl deoxycholate

Produkt 1

HCID 52840625beta-Cholane-3alpha,12alpha,24-triolAusbeute 103,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A suspension of LiA1H4 (0.15 g, 3 mols. equiv.) in dry THF (25 ml) was stirred under nitrogen whilst standing in an ice/methanol bath. Methyl deoxycholate (5b) (0.5 g, 1.2 mmol) in dry THF (30 ml) was then added dropwise and the resultant mixture stirred at ambient temperature for 2.5 hours. Water was then introduced carefully to the mixture until all the excess LiA1H4 had been destroyed. The resultant mixture was acidified with 2M HCl and extracted into EtOAc (3×). The combined organic extracts were washed with water (2×), dried and evaporated to give a white foam (0.47 g, 100%). Recrystallisation of 0.41 g from ethyl acetate afforded pure 3α,12α,24-trihydroxy-5β-cholane (7b)8 (0.30 g, 73%): m.p. 110°-116° C. [Lit8 107°-114° C.); 1H nmr (90 MHz; CDCl3 /DMSO d6) δ 0.67 (3H, s, 18-CH3), 0.90 (3H, s, 19-CH3), 3.2-3.7 (1H, m, 3β-H), 3.4-3.6 (2H, t(broadened), 24-CH2), 3.8-4.0 (1H, m, 12β-H); IR (KBr) 3366 (OH's) cm-1.

Aufarbeitung

  1. customwhilst standing in an ice/methanol bath
  2. customhad been destroyed
  3. extractionextracted into EtOAc (3×)
  4. washThe combined organic extracts were washed with water (2×)
  5. customdried
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-820995e12df64472a36ea4cb3c901df5
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05304551

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