Hexamethyldisilazane → HCID 58506468, compound

HRID 2167292Notes

Reaction equation

HRID 2167292 reaction equation
C[Si](C)(C)N[Si](C)(C)C.C([Li])CCC.[C:15]([N:23]1[CH:27]([CH3:28])[C:26](=[O:29])[O:25][CH:24]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Br[CH2:37][N:38]1[C:42](=[O:43])[C:41]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:40]2[C:39]1=[O:48]>C1COCC1>[C:15]([N:23]1[C:27]([CH2:37][N:38]2[C:42](=[O:43])[C:41]3[C:40](=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:39]2=[O:48])([CH3:28])[C:26](=[O:29])[O:25][CH:24]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 13838HexamethyldisilazaneHCID 792441H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)-HCID 13818179HCID 13818179, compoundHCID 178418339Butyllithium

Product 1

HCID 58506468HCID 58506468, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Into a solution of hexamethyldisilazane (17.5 g, 106 mmol) in THF (100 mL) was added n-butyllithium (1.58 M in hexane, 50 mL, 78.5 mmol) at −78° C. After 5 min at −78° C., the solution was allowed to warm to 0° C. for 30 min and then cooled to −78° C. again. A solution of 3-benzoyl-4-methyl-2-phenyl-1,3-oxazolidin-5-one (dried overnight in vacuo before using, 20 g, 71 mmol) in THF (250 mL) was added slowly under argon, and the dark red brown solution was stirred at this temperature for 3 h. A solution of N-(bromomethyl)phthalimide (22.2 g, 92.5 mmol) in THF (200 mL) was then added dropwise. The reaction mixture was allowed to warm to 20° C. in 4 h and stirred at this temperature overnight. The solvent was evaporated. The residue was dissolved in 10% NH4Cl (250 mL) and extracted with CH2Cl2. The organic phase was dried over Na2SO4 and evaporated. Recrystallization from CH2Cl2 and ether (1:4) gave white crystals of 2-((3-benzoyl-4-methyl-5-oxo-2-phenyloxazolidin-4-yl)methyl)isoindoline-1,3-dione (23 g, 74%). LC-MS (ES, m/z): 441 [M+H]+.

Workup

  1. temperaturecooled to −78° C. again
  2. temperatureto warm to 20° C. in 4 h
  3. stirringstirred at this temperature overnight
  4. customThe solvent was evaporated
  5. dissolutionThe residue was dissolved in 10% NH4Cl (250 mL)
  6. extractionextracted with CH2Cl2
  7. dry with materialThe organic phase was dried over Na2SO4
  8. customevaporated
  9. customRecrystallization from CH2Cl2 and ether (1:4)

Sources & evidence

ORD record
ord-1f89f56c2d1b4abbbd61a02ea3eadf47
Source dataset
uspto-grants-2015_06
Patent number
US09045440B2

Reaction notes

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