Chlorotrimethylsilane → HCID 67784482, compound

HRID 2210712Notes

Reaction equation

HRID 2210712 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[Si:13]([N:20]1[C@H:23]([CH:24]2[C:29](=[O:30])[CH2:28][CH2:27][CH2:26][O:25]2)[C@@H:22]([C@H:31]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH3:32])[C:21]1=[O:41])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].[CH3:42][Si:43]([CH3:46])([CH3:45])Cl.[Cl-].[NH4+]>C1COCC1>[Si:13]([N:20]1[C@H:23]([C@@H:24]2[C:29]([O:30][Si:43]([CH3:46])([CH3:45])[CH3:42])=[CH:28][CH2:27][CH2:26][O:25]2)[C@@H:22]([C@H:31]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:35])[CH3:36])[CH3:32])[C:21]1=[O:41])([C:16]([CH3:17])([CH3:19])[CH3:18])([CH3:15])[CH3:14]

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 67783615HCID 67783615, compoundHCID 178418339Butyllithium

Product 1

HCID 67784482HCID 67784482, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of diisopropylamine (0.294 ml) in dry THF (5 ml) was added butyllithium (1.25 ml, 1.6M in hexane) dropwise at 0° C. and the mixture was stirred for 10 minutes. This solution was cooled to -78° C. and a solution of (3S,4S)-1-(tert-butyldimethylsilyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(2RS)-3-oxotetrahydropyran-2-yl)azetidin-2-one (441 mg) in dry THF (2 ml) was added dropwise. The mixture was stirred for 30 minutes, after which trimethylchlorosilane (0.267 ml) was added. This mixture was stirred at -20° C. for 10 minutes. The reaction mixture was then poured in a saturated aqueous solution of ammonium chloride (20 ml) and extracted with ether (20 ml). The organic layer was washed successively with water (20 ml), 2% HCl (20 ml), saturated aqueous sodium hydrogen carbonate (20 ml) and saturated aqueous sodium chloride (20 ml). The extract was then dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. Finally, the residue was purified by silica gel column chromatography (230-400 mesh, 26 g; ethyl acetate-hexane=1:15) to give (3S,4S)-1-(tert-butyldimethylsilyl)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(2R)-3-trimethylsilyloxy-5,6-dihydropyran-2-yl]azetidin-2-one (228 mg) as a colorless oil.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. stirringThis mixture was stirred at -20° C. for 10 minutes
  3. extractionextracted with ether (20 ml)
  4. washThe organic layer was washed successively with water (20 ml), 2% HCl (20 ml), saturated aqueous sodium hydrogen carbonate (20 ml) and saturated aqueous sodium chloride (20 ml)
  5. dry with materialThe extract was then dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customFinally, the residue was purified by silica gel column chromatography (230-400 mesh, 26 g; ethyl acetate-hexane=1:15)

Sources & evidence

ORD record
ord-b9a3c3e1d09d4f16b4722b400e158bd2
Source dataset
uspto-grants-1995_10
Patent number
US05459260

Reaction notes

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