HCID 18605984, compound → HCID 57085025, compound

HRID 1906687Notes

Reaction equation

HRID 1906687 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 18605984HCID 18605984, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 57085025HCID 57085025, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.033 g. (0.00088 mole) of lithium aluminum hydride, 4 ml. of tetrahydrofuran, and 0.223 g. (0.00026 mole) of [1α,3β,24S]-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 12 ml. of ether and quenched with the dropwise addition of 0.07 ml. of water and 0.05 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,24S]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24-fluorocholest-5-ene.

Workup

  1. additionA mixture of 0.033 g
  2. temperaturecooled to 0° C
  3. additionThe mixture was diluted with 12 ml
  4. customof ether and quenched with the dropwise addition of 0.07 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-20639c0a841641c69ac48a464b31a8aa
Source dataset
uspto-grants-1987_03
Patent number
US04652405

Reaction notes

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