N,N-Dimethylmethanesulphonamide → HCID 68631790, compound

HRID 1160141Notes

Reaction equation

HRID 1160141 reaction equation
C([Li])CCC.[CH3:6][N:7]([CH3:12])[S:8]([CH3:11])(=[O:10])=[O:9].[C:13]1(=[N:19][S:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C1COCC1>[CH3:6][N:7]([CH3:12])[S:8]([CH2:11][C:13]1([NH:19][S:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 70191N,N-DimethylmethanesulphonamideHCID 58591374729559-16-4HCID 178418339Butyllithium

Product 1

HCID 68631790HCID 68631790, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (1.3 eq, 8.07 mL of a 1.6M soln in hexanes) was added dropwise to a cooled (−78° C.) solution of N,N-dimethyl methanesulfonamide (1.35 eq, 1.65 g) in 100 mL of dry THF under anhydrous atmosphere. The mixture was stirred for 30 min at that temperature and then transferred via cannula to a solution of sulfinyl imine 1200-B (2.0 g) in 100 mL of dry THF at −78° C. After addition was completed, the reaction mixture was stirred for 1 h. The reaction was quenched at −78° C. by addition of 20 mL of aqueous saturated ammonium chloride solution. The mixture was allowed to reach room temp and then partitioned between dichloromethane (300 mL) and aqueous saturated sodium bicarbonate solution (300 mL). The aqueous layer was back extracted with dichloromethane (2×200 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated. The residue was chromatographed on silica gel (gradient:dichloromethane/hexanes; 1:1 to 30% acetone in dichloromethane/hexanes; 1:1) to afford the product 1200-C (1.36 g; 42%) as a colorless oil.

Workup

  1. additionAfter addition
  2. stirringthe reaction mixture was stirred for 1 h
  3. customThe reaction was quenched at −78° C. by addition of 20 mL of aqueous saturated ammonium chloride solution
  4. customto reach room temp
  5. custompartitioned between dichloromethane (300 mL) and aqueous saturated sodium bicarbonate solution (300 mL)
  6. extractionThe aqueous layer was back extracted with dichloromethane (2×200 mL)
  7. dry with materialThe combined organic layers were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel (gradient:dichloromethane/hexanes; 1:1 to 30% acetone in dichloromethane/hexanes; 1:1)

Sources & evidence

ORD record
ord-cebb63673238487bb9953b5051e9d926
Source dataset
uspto-grants-2010_10
Patent number
US07816326B2

Reaction notes

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