Cholic Acid → HCID 101785466, compound

HRID 1526668Notes

Reaction equation

HRID 1526668 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C@@H:8]([C@@H:14]1[C@@:18]2([CH3:35])[C@@H:19]([OH:34])[CH2:20][C@@H:21]3[C@@:26]4([CH3:32])[CH2:27][CH2:28][C@@H:29]([OH:31])[CH2:30][C@H:25]4[CH2:24][C@@H:23]([OH:33])[C@H:22]3[C@@H:17]2[CH2:16][CH2:15]1)[CH2:9][CH2:10][C:11](O)=[O:12]>C1COCC1>[OH:31][C@@H:29]1[CH2:28][CH2:27][C@@:26]2([CH3:32])[CH:25]([CH2:24][C@@H:23]([OH:33])[C@@H:22]3[C@@H:21]2[CH2:20][C@H:19]([OH:34])[C@@:18]2([CH3:35])[C@H:17]3[CH2:16][CH2:15][C@@H:14]2[C@H:8]([CH3:7])[CH2:9][CH2:10][CH2:11][OH:12])[CH2:30]1

Participants

4

Reactant 2

HCID 221493Cholic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 101785466HCID 101785466, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (3.85 g, 100 mmol) in dry THF (100 mL) at 0° C. was added dropwise a solution of cholic acid (15.03 g, 35 mmol) in dry THF (200 mL) with vigorous stirring under nitrogen atmosphere. The reaction mixture was then heated to reflux with stirring for overnight. Upon completion, the reaction was carefully quenched with saturated aqueous NH4Cl solution at RT. Then the mixture was acidified with IN HCl to pH 1˜2. The precipitate was collected via filtration and washed with water and acetone to give the product (12.1 g, 88%) as a white solid.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux
  3. stirringwith stirring for overnight
  4. customUpon completion, the reaction was carefully quenched with saturated aqueous NH4Cl solution at RT
  5. filtrationThe precipitate was collected via filtration
  6. washwashed with water and acetone

Sources & evidence

ORD record
ord-d80a5930a3ce4013a1c30bf30081d5a8
Source dataset
uspto-grants-2015_07
Patent number
US09085602B1

Reaction notes

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