Tetrahydrofuran → HCID 18605985, compound

HRID 1906680Notes

Reaction equation

HRID 1906680 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.C([O:14][C:15](=O)[C@@H:16]([C@@H:30]1[C@:47]2([CH3:48])[C@H:33]([C@H:34]3[C@H:44]([CH2:45][CH2:46]2)[C@:42]2([CH3:43])[C:37]([CH2:38][C@@H:39]([O:56][CH:57]4[CH2:62][CH2:61][CH2:60][CH2:59][O:58]4)[CH2:40][C@@H:41]2[O:49][CH:50]2[CH2:55][CH2:54][CH2:53][CH2:52][O:51]2)=[CH:36][CH2:35]3)[CH2:32][CH2:31]1)[CH2:17][CH2:18][C@H:19]([F:29])[C:20]([O:23][CH:24]([O:26][CH2:27][CH3:28])[CH3:25])([CH3:22])[CH3:21])C>CCOCC>[O:51]1[CH2:52][CH2:53][CH2:54][CH2:55][CH:50]1[O:49][C@@H:41]1[C@@:42]2([CH3:43])[C:37](=[CH:36][CH2:35][C@@H:34]3[C@@H:44]2[CH2:45][CH2:46][C@@:47]2([CH3:48])[C@H:33]3[CH2:32][CH2:31][C@@H:30]2[C@H:16]([CH2:15][OH:14])[CH2:17][CH2:18][C@H:19]([F:29])[C:20]([O:23][CH:24]([O:26][CH2:27][CH3:28])[CH3:25])([CH3:22])[CH3:21])[CH2:38][C@@H:39]([O:56][CH:57]2[CH2:62][CH2:61][CH2:60][CH2:59][O:58]2)[CH2:40]1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 57146700HCID 57146700, compound

Product 1

HCID 18605985HCID 18605985, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 0.028 g. (0.00074 mole) of lithium aluminum hydride in 1 ml. of tetrahydrofuran at 0° C. was added 0.200 g. (0.00027 mole) of [1α,3β,24S]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24-fluorocholest-5-en-21-oic acid ethyl ester in 3 ml. of tetrahydrofuran. The mixture was stirred at 50° C. for 1.5 hr, recooled to 0° C. and diluted with 12 ml. of ether. The mixture was then quenched with the dropwise addition of 0.06 ml. of water and 0.05 ml. of 10% aqueous sodium hydroxide. The mixture was stirred at 25° C. for 0.5 hr and was filtered. The solids were triturated with ether and filtered. Evaporation of solvent afforded [1α,3β,24S]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24-fluorocholest-5-en-21-ol.

Workup

  1. additionTo a mixture of 0.028 g
  2. customrecooled to 0° C.
  3. additiondiluted with 12 ml
  4. customThe mixture was then quenched with the dropwise addition of 0.06 ml
  5. stirringThe mixture was stirred at 25° C. for 0.5 hr
  6. filtrationwas filtered
  7. customThe solids were triturated with ether
  8. filtrationfiltered
  9. customEvaporation of solvent

Sources & evidence

ORD record
ord-939821d599df41ed8f10483c21a8b5e6
Source dataset
uspto-grants-1987_03
Patent number
US04652405

Reaction notes

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