HCID 70213398, compound → HCID 70215948, compound

HRID 566892Notes

Reaction equation

HRID 566892 reaction equation
COC[O:4][C@@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:26]2[CH2:25][C@H:24]([O:31]COC)[C@@:23]2([CH3:35])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][C:18]([CH3:21])([CH3:20])[OH:19])[CH2:6]1>C1COCC1>[OH:4][C@@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:26]2[CH2:25][C@H:24]([OH:31])[C@@:23]2([CH3:35])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][C:18]([CH3:21])([CH3:20])[OH:19])[CH2:6]1

Participants

3

Reactant 1

HCID 70213398HCID 70213398, compound

Product 1

HCID 70215948HCID 70215948, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the crude alcohol in 60 mL of THF and 18 mL of 2 M liCl was refluxed for 24 h. After the solution was concentrated to about 20 mL and diluted with about 50 mL of ether, it was washed with 50 mL of water, 50 mL of saturated NaCHO3 2 and 50 mL of brine respectively. The solution was dried over anhydrous MgSO4 and concentrated to afford crude 3α,12α-dihydroxy-24,24-dimethyl-5α-cholan-24-ol.

Workup

  1. concentrationAfter the solution was concentrated to about 20 mL
  2. additiondiluted with about 50 mL of ether, it
  3. washwas washed with 50 mL of water, 50 mL of saturated NaCHO3 2 and 50 mL of brine respectively
  4. dry with materialThe solution was dried over anhydrous MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2893101d143441b98255fae5ab4bf731
Source dataset
uspto-grants-2001_01
Patent number
US06177417B1

Reaction notes

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