HCID 13189262, compound → HCID 13189266, compound

HRID 434512Notes

Reaction equation

HRID 434512 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C@@H:11]([C@@H:26]1[C@:43]2([CH3:44])[C@H:29]([C@H:30]3[C@H:40]([CH2:41][CH2:42]2)[C@:38]2([CH3:39])[C:33]([CH2:34][C@@H:35]([O:52][CH:53]4[CH2:58][CH2:57][CH2:56][CH2:55][O:54]4)[CH2:36][C@@H:37]2[O:45][CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][O:47]2)=[CH:32][CH2:31]3)[CH2:28][CH2:27]1)[CH2:12][CH2:13][C:14]([F:25])([F:24])[C:15]([O:18][CH:19]([O:21][CH2:22][CH3:23])[CH3:20])([CH3:17])[CH3:16])C>O1CCCC1.CCOCC>[O:47]1[CH2:48][CH2:49][CH2:50][CH2:51][CH:46]1[O:45][C@@H:37]1[C@@:38]2([CH3:39])[C:33](=[CH:32][CH2:31][C@@H:30]3[C@@H:40]2[CH2:41][CH2:42][C@@:43]2([CH3:44])[C@H:29]3[CH2:28][CH2:27][C@@H:26]2[C@H:11]([CH2:10][OH:9])[CH2:12][CH2:13][C:14]([F:24])([F:25])[C:15]([O:18][CH:19]([O:21][CH2:22][CH3:23])[CH3:20])([CH3:17])[CH3:16])[CH2:34][C@@H:35]([O:52][CH:53]2[CH2:58][CH2:57][CH2:56][CH2:55][O:54]2)[CH2:36]1

Participants

5

Reactant 2

HCID 13189262HCID 13189262, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13189266HCID 13189266, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a mixture of 0.20 g (0.0053 mol) of lithium aluminum hydride and 10 mL of tetrahydrofuran at 0° C. was added 2.55 g (0.0034 mol) of [1α,3β]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24,24-difluorocholest-5-en-21-oic acid ethyl ester in 35 mL of tetrahydrofuran. The mixture was heated at 50° C. for 1.5 hr, recooled to 0° C., and diluted with 120 mL of ether. The mixture was then quenched with the dropwise addition of 0.40 ml of water and 0.32 mL of 10% aqueous sodium hydroxide. The mixture was stirred at 25° C. for 1 hr and was filtered. The solids were triturated with ether and filtered. Evaporation of solvent afforded [1α,3β]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24,24-difluorocholest-5-en-21ol, [α]D20 +4° (c 1, CHCl3).

Workup

  1. customrecooled to 0° C.
  2. customThe mixture was then quenched with the dropwise addition of 0.40 ml of water and 0.32 mL of 10% aqueous sodium hydroxide
  3. filtrationwas filtered
  4. customThe solids were triturated with ether
  5. filtrationfiltered
  6. customEvaporation of solvent

Sources & evidence

ORD record
ord-3e53c74d6320425ba0265c6ec26dc774
Source dataset
uspto-grants-1983_08
Patent number
US04397847

Reaction notes

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