Lithocholic Acid → 5-(2-Adamantylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 1420483Notes

Reaction equation

HRID 1420483 reaction equation
C[C@@H]([C@@H:8]1[C@@:12]2(C)[C@@H](O)C[C@@H:15]3[C@@:20]4(C)[CH2:21][CH2:22][C@@H:23]([OH:25])C[C@H:19]4[CH2:18][CH2:17][C@H:16]3[C@@H:11]2CC1)CCC(O)=O.C[C@@H]([C@@H]1[C@@]2(C)CC[C@@H]3[C@@]4(C)C[CH2:50][C@@H:51]([OH:53])[CH2:52][C@H]4CC[C@H]3[C@@H]2CC1)CCC(O)=O.C12([C:66]([OH:68])=[O:67])CC3CC(CC(C3)C1)C2.[Mn]([O-])(=O)(=O)=O.[K+].[OH-].[Na+]>>[CH:12]12[CH2:8][CH:18]3[CH2:17][CH:16]([CH2:15][CH:20]([CH2:19]3)[C:21]1=[C:22]1[C:23](=[O:25])[O:53][C:51]([CH3:50])([CH3:52])[O:68][C:66]1=[O:67])[CH2:11]2

Participants

6

Reactant 5

HCID 9903Lithocholic Acid2×HCID 132351-Adamantanecarboxylic acid3×HCID 14798Sodium HydroxideHCID 222528Deoxycholic Acid2×HCID 516875Potassium Permanganate

Product 1

HCID 7264755-(2-Adamantylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Procedure

As a compound containing both carboxylic acid and hydroxyl group, deoxycholic acid (Compound I, Aldrich reagent) and lithocholic acid (Compound J, Aldrich reagent) were employed. 1-adamantane carboxylic acid was oxidized by making use of an aqueous solution of potassium permanganate, and then mixed with an aqueous solution of sodium hydroxide to synthesized adamantane 1-carboxylic acid 3-ol (Compound K).

Sources & evidence

ORD record
ord-bee8bd4ad0c346788d6fe1a42b08d16e
Source dataset
uspto-grants-2000_06
Patent number
US06071670

Reaction notes

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