Apocholic acid → HCID 67857083, compound

HRID 1587033Notes

Reaction equation

HRID 1587033 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][C@@H:8]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@H:10]([CH2:11][CH2:12][C:13]3[C@@H:28]2[CH2:27][C@H:26]([OH:33])[C@@:25]2([CH3:34])[C:14]=3[CH2:15][CH2:16][C@@H:17]2[C@H:18]([CH3:24])[CH2:19][CH2:20][C:21](O)=[O:22])[CH2:9]1>O1CCCC1>[OH:7][C@@H:8]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@H:10]([CH2:11][CH2:12][C:13]3[C@@H:28]2[CH2:27][C@H:26]([OH:33])[C@@:25]2([CH3:34])[C:14]=3[CH2:15][CH2:16][C@@H:17]2[C@H:18]([CH3:24])[CH2:19][CH2:20][CH2:21][OH:22])[CH2:9]1

Participants

4

Reactant 2

HCID 101818Apocholic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 67857083HCID 67857083, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of lithium aluminum hydride (6.7 g) in tetrahydrofuran (50 ml) is cooled to 0° C. and a solution of 3α, 12α-dihydroxy-5β-chol-8(14)-en-24-oic acid (15.3 g) in tetrahydrofuran (350 ml) is added to dropwise. The mixture is warmed to room temperature, stirred for about 17 hours, and quenched by dropwise addition of water (6.7 ml), 15% sodium hydroxide solution (6.7 ml), and water (6.7 ml). The mixture is filtered, washing the alumina salts with 20% ethanol in ethyl acetate, and the filtrate concentrated in vacuo to give the desired product which is used, without further treatment, for the next step.

Workup

  1. temperatureThe mixture is warmed to room temperature
  2. customquenched by dropwise addition of water (6.7 ml), 15% sodium hydroxide solution (6.7 ml), and water (6.7 ml)
  3. filtrationThe mixture is filtered
  4. washwashing the alumina salts with 20% ethanol in ethyl acetate
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-667cda3d3dc2435fb6b69a38e40ce521
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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