N-Methoxy-N-methylbutyramide → HCID 71284529, compound

HRID 1481726Notes

Reaction equation

HRID 1481726 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH:13]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C:6]3=[CH:5][C:4]=2[CH:3]=1.[Li]CCCC.CON(C)[C:30](=[O:34])[CH2:31][CH2:32][CH3:33]>C1COCC1>[Si:15]([O:14][CH:13]1[C:6]2=[CH:5][C:4]3[CH:3]=[C:2]([C:30](=[O:34])[CH2:31][CH2:32][CH3:33])[CH:10]=[CH:9][C:8]=3[N:7]2[CH2:11][CH2:12]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 13704543N-Methoxy-N-methylbutyramideHCID 71285448HCID 71285448, compoundHCID 178418339Butyllithium

Product 1

HCID 71284529HCID 71284529, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-bromo-1-(tert-butyldimethylsilyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indole (4.1 g, 11.2 mmol) in THF (60 mL), cooled to −78° C., was added n-BuLi (7.7 mL, 1.6M, 12.3 mmol) dropwise. The reaction mixture was allowed to stir at −78° C. for 5 minutes before N-methoxy-N-methylbutyramide (1.6 g, 12.3 mmol) was added. The resulting orange solution was allowed to slowly warm to room temperature then quenched with the addition of a saturated solution of NH4Cl. The reaction mixture was poured into H2O (100 mL) and extracted with Et2O (2×100 mL). The combined organic phases were dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound as a white solid (4.0 g, 99%).

Workup

  1. additionwas added
  2. customthen quenched with the addition of a saturated solution of NH4Cl
  3. additionThe reaction mixture was poured into H2O (100 mL)
  4. extractionextracted with Et2O (2×100 mL)
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-44b3ee8efeb845bba0b2377989f3d606
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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