Chlorotrimethylsilane → HCID 66594479, compound

HRID 424436Notes

Reaction equation

HRID 424436 reaction equation
Cl[Si](C)(C)C.[BH4-].[Li+].CS([O:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]2[O:24][CH2:23][C:22](=O)[N:21]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:20]2)=[CH:15][CH:14]=1)(=O)=O.[OH-].[K+]>O1CCCC1.C(O)C.O.CO>[CH2:26]([N:21]1[CH2:22][CH2:23][O:24][C@@H:19]([C:16]2[CH:15]=[CH:14][C:13]([OH:12])=[CH:18][CH:17]=2)[CH2:20]1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

9

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 14797Potassium HydroxideHCID 4148881Lithium borohydrideHCID 86630238HCID 86630238, compound

Product 1

HCID 66594479HCID 66594479, compoundYield 67%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Chlorotrimethylsilane (96 g, 884 mmol) was added to a solution of lithium borohydride (9.6 g, 441 mmol) in tetrahydrofuran (500 ml) and stirred for one hour at room temperature. A solution of 4-((2S)-4-benzyl-5-oxo-morpholin-2-yl)phenyl methanesulfonate (79.8 g, 221 mmol) in tetrahydrofuran (200 ml) was added to the solution and stirred at room temperature for one hour. After careful addition of methanol (60 ml) under ice-cooling, the solvent was removed under reduced pressure. Potassium hydroxide (145 g, 2.2 mol) was added to a solution of the residue in ethanol (300 ml) and water (300 ml) and the mixture was stirred at 80° C. for 2 hours. The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. Removal of the solvent yielded (2S)-4-benzyl-2-(4-hydroxyphenyl)morpholine (39.8 g, 67%) as white crystals.

Workup

  1. stirringstirred at room temperature for one hour
  2. temperaturecooling
  3. customthe solvent was removed under reduced pressure
  4. customThe solvent was removed under reduced pressure
  5. extractionthe residue was extracted with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-f8faf6f578de4ef5baedaee50a8f2a2e
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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