HCID 13826515, compound → HCID 13826517, compound

HRID 1906685Notes

Reaction equation

HRID 1906685 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CC1C=CC(S(O[CH2:18][C@@H:19]([C@@H:33]2[C@:50]3([CH3:51])[C@H:36]([C@H:37]4[C@H:47]([CH2:48][CH2:49]3)[C@:45]3([CH3:46])[C:40]([CH2:41][C@@H:42]([O:59][CH:60]5[CH2:65][CH2:64][CH2:63][CH2:62][O:61]5)[CH2:43][C@@H:44]3[O:52][CH:53]3[CH2:58][CH2:57][CH2:56][CH2:55][O:54]3)=[CH:39][CH2:38]4)[CH2:35][CH2:34]2)[CH2:20][CH2:21][C@@H:22]([F:32])[C:23]([O:26][CH:27]([O:29][CH2:30][CH3:31])[CH3:28])([CH3:25])[CH3:24])(=O)=O)=CC=1>O1CCCC1>[O:54]1[CH2:55][CH2:56][CH2:57][CH2:58][CH:53]1[O:52][C@@H:44]1[C@@:45]2([CH3:46])[C:40](=[CH:39][CH2:38][C@@H:37]3[C@@H:47]2[CH2:48][CH2:49][C@@:50]2([CH3:51])[C@H:36]3[CH2:35][CH2:34][C@@H:33]2[C@H:19]([CH3:18])[CH2:20][CH2:21][C@@H:22]([F:32])[C:23]([O:26][CH:27]([O:29][CH2:30][CH3:31])[CH3:28])([CH3:25])[CH3:24])[CH2:41][C@@H:42]([O:59][CH:60]2[CH2:65][CH2:64][CH2:63][CH2:62][O:61]2)[CH2:43]1

Participants

4

Reactant 2

HCID 13826515HCID 13826515, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13826517HCID 13826517, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.710 g. (0.0187 mole) of lithium aluminum hydride, 80 ml. of tetrahydrofuran and 4.85 g. (0.0057 mole) of [1α,3β,24R]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24-fluorocholest-5-en-21-ol 21-(4-methylbenzenesulfonate) was heated at reflux (60° C.) for 1 hr and cooled to 0° C. The mixture was diluted with 200 ml. of ether and quenched with the dropwise addition of 1.4 ml. of water and 1.1 ml. of 10% aqueous sodium hydroxide solution. The mixture was then stirred for 1 hr and filtered. The solids were triturated with ether and filtered. The combined filtrates were evaporated to dryness and chromatographed on 0.06-0.20 mm silica gel to yield [1α,3β,24R]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24-fluorocholest-5-ene, [α]D20 +7° (c 1, CHCl3 ).

Workup

  1. additionA mixture of 0.710 g
  2. temperaturecooled to 0° C
  3. additionThe mixture was diluted with 200 ml
  4. customof ether and quenched with the dropwise addition of 1.4 ml
  5. filtrationfiltered
  6. customThe solids were triturated with ether
  7. filtrationfiltered
  8. customThe combined filtrates were evaporated to dryness
  9. customchromatographed on 0.06-0.20 mm silica gel

Sources & evidence

ORD record
ord-365f301129d64026b240b5668ace7b18
Source dataset
uspto-grants-1987_03
Patent number
US04652405

Reaction notes

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