Sodium bis(2-methoxyethoxy)aluminiumhydride → HCID 22481034, compound

HRID 412683Notes

Reaction equation

HRID 412683 reaction equation
[H-].[H-].COCCO[Al+]OCCOC.[Na+].[Si:15]([O:22][CH:23]1[CH2:32][C:31]([CH3:34])([CH3:33])[CH2:30][C:29]2[N:28]=[C:27]([CH:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[C:26]([C:40]([C:42]3[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:44][CH:43]=3)=[O:41])=[C:25]([C:52]3[CH:57]=[CH:56][C:55]([F:58])=[C:54]([F:59])[CH:53]=3)[C:24]1=2)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>C1(C)C=CC=CC=1>[Si:15]([O:22][CH:23]1[CH2:32][C:31]([CH3:34])([CH3:33])[CH2:30][C:29]2[N:28]=[C:27]([CH:35]3[CH2:36][CH2:37][CH2:38][CH2:39]3)[C:26]([CH:40]([C:42]3[CH:43]=[CH:44][C:45]([C:48]([F:51])([F:49])[F:50])=[CH:46][CH:47]=3)[OH:41])=[C:25]([C:52]3[CH:57]=[CH:56][C:55]([F:58])=[C:54]([F:59])[CH:53]=3)[C:24]1=2)([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 22481033HCID 22481033, compound

Product 1

HCID 22481034HCID 22481034, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At 0° C., 1.15 ml (4 mmol) of sodium bis-(2-methoxyethoxy)-aluminium dihydride (65% strength in toluene) were added dropwise to 600 mg (0.93 mmol) of [5-(tert-butyldimethylsilanyloxy)-2-cyclopentyl-4-(3,4-difluorophenyl)-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-3-yl]-(4-trifluoromethylphenyl)-methanone dissolved in 6 ml of toluene. After 3.5 hours, the reaction was quenched with methanol, the mixture was extracted with ethyl acetate and the organic phase was washed with potassium-sodium tartrate solution and saturated aqueous sodium bicarbonate solution and dried. The solvent is distilled off under reduced pressure and the residue is then purified over a silica gel column using toluene/ethyl acetate. This gives a total of 0.56 g of a colourless foam.

Workup

  1. customthe reaction was quenched with methanol
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with potassium-sodium tartrate solution and saturated aqueous sodium bicarbonate solution
  4. customdried
  5. distillationThe solvent is distilled off under reduced pressure
  6. customthe residue is then purified over a silica gel column

Sources & evidence

ORD record
ord-ab39b770851849269624967b2bcd55ff
Source dataset
uspto-grants-2003_05
Patent number
US06562976B2

Reaction notes

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