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

HRID 1464250노트

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HRID 1464250 반응식
[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

참가 물질

4

반응물 2

HCID 962WaterHCID 229346Methyl deoxycholate

생성물 1

HCID 52840625beta-Cholane-3alpha,12alpha,24-triol수율 103.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-820995e12df64472a36ea4cb3c901df5
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05304551

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