Dehydrolithocholic Acid → Lithocholic Acid

HRID 481117

반응식

HRID 481117 반응식
[O:1]=[C:2]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:22]2[CH2:21][CH2:20][C@@:19]2([CH3:27])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:18])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:3]1.C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>O1CCCC1>[CH3:18][C@@H:12]([C@@H:11]1[C@@:19]2([CH3:27])[CH2:20][CH2:21][C@@H:22]3[C@@:23]4([CH3:26])[CH2:24][CH2:25][C@@H:2]([OH:1])[CH2:3][C@H:4]4[CH2:5][CH2:6][C@H:7]3[C@@H:8]2[CH2:9][CH2:10]1)[CH2:13][CH2:14][C:15]([OH:17])=[O:16]

참가 물질

4

반응물 2

HCID 5283906Dehydrolithocholic AcidHCID 16684435Lithium tritertbutoxyaluminohydride

생성물 1

HCID 9903Lithocholic Acid수율 99.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

3-Oxo-5β-cholan-24-oic acid (3.0 g) was dissolved in dry tetrahydrofuran (40 ml), cooled on an ice-bath, and over 15 min. 17.5 ml of 1.1 M solution of Lithium tri-tert-butoxyaluminohydride was added with stirring. Further 10 ml of tetrahydrofuran was added and stirring was continued for 15 min on an ice-bath and 1.5 hours at room temperature. After cooling the mixture on an ice-bath, the reaction was quenched by addition of 16 ml of water, followed by 20 ml of 6M HCl. The mixture was extracted with dichloromethane and the combined organic phases were washed with 1 M HCl and water and dried (Na2SO4). Removal of the solvent under reduced pressure gave 3.0 g of crude lithocholic acid. NMR analysis (CDCl3, 300 MHz) of the product showed characteristic signal at 0.66 (3H,s); 0.93 (6H, s and d); 2.15-2.49 (2H, m); 3.63 (1H, m), in accordance with the 1H-NMR spectrum of reference lithocholic acid.

후처리

  1. temperaturecooled on an ice-bath
  2. stirringstirring
  3. waitwas continued for 15 min on an ice-bath and 1.5 hours at room temperature
  4. temperatureAfter cooling the mixture on an ice-bath
  5. customthe reaction was quenched by addition of 16 ml of water
  6. extractionThe mixture was extracted with dichloromethane
  7. washthe combined organic phases were washed with 1 M HCl and water
  8. dry with materialdried (Na2SO4)
  9. customRemoval of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-9d3b1703e32942bcbc15540397563255
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06653492B2

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