Lithium Hydroxide → HCID 54759583, compound

HRID 405088Notes

Reaction equation

HRID 405088 reaction equation
C([O:9][CH2:10][C@:11]12[CH2:49][CH2:48][C@@H:47]([C:50]([CH3:52])=[CH2:51])[C@@H:12]1[C@@H:13]1[C@@:26]([CH3:29])([CH2:27][CH2:28]2)[C@@:25]2([CH3:30])[C@@H:16]([C@:17]3([CH3:46])[C@@H:22]([CH2:23][CH2:24]2)[C:21]([CH3:32])([CH3:31])[C:20]([C:33]2[CH:45]=[CH:44][C:36]([C:37]([O:39]C(C)(C)C)=[O:38])=[CH:35][CH:34]=2)=[CH:19][CH2:18]3)[CH2:15][CH2:14]1)(=O)C1C=CC=CC=1.[OH-].[Li+]>O1CCOCC1.O>[OH:9][CH2:10][C@:11]12[CH2:49][CH2:48][C@@H:47]([C:50]([CH3:52])=[CH2:51])[C@@H:12]1[C@@H:13]1[C@@:26]([CH3:29])([CH2:27][CH2:28]2)[C@@:25]2([CH3:30])[C@@H:16]([C@:17]3([CH3:46])[C@@H:22]([CH2:23][CH2:24]2)[C:21]([CH3:32])([CH3:31])[C:20]([C:33]2[CH:45]=[CH:44][C:36]([C:37]([OH:39])=[O:38])=[CH:35][CH:34]=2)=[CH:19][CH2:18]3)[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86676414HCID 86676414, compound

Product 1

HCID 54759583HCID 54759583, compoundYield 39.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
75 °C

Procedure

To a solution of tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(benzoyloxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (7.2 g, 10.21 mmol) in 1,4-dioxane (75 ml) and water (25 ml) was added lithium hydroxide (1.285 g, 30.6 mmol) and the mixture was stirred at 75° C. Dioxane (50 ml) was added to dissolve all solids and the stirring was continued for 24 h. The solvent was removed and the residue was redissolved into CH2Cl2, the insoluble white solid was collected to afford 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid (2.2 g, 39.5%) LCMS: m/e 545.4 (MH+), 2.68 min (method 2).

Workup

  1. dissolutionto dissolve all solids
  2. customThe solvent was removed
  3. dissolutionthe residue was redissolved into CH2Cl2
  4. customthe insoluble white solid was collected

Sources & evidence

ORD record
ord-d39fd0d94e65478393bd7710c0a49cc2
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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