1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(6-benzyloxy-2,2-dimethyl-2H-chromen-4-yl)-N-methyl-methanesulfonamide

HRID 613441Notes

Reaction equation

HRID 613441 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH:13](OC(=O)C)[CH:12]2[N:25]([CH3:30])[S:26]([CH3:29])(=[O:28])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.CC(=O)OCC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([CH3:20])([CH3:19])[CH:13]=[C:12]2[N:25]([CH3:30])[S:26]([CH3:29])(=[O:27])=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11048325N-(6-benzyloxy-3-acetoxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide

Product 1

HCID 9842492N-(6-benzyloxy-2,2-dimethyl-2H-chromen-4-yl)-N-methyl-methanesulfonamideYield 99%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.0 g (2.3 mmol) of N-(6-benzyloxy-3-acetoxy-2,2-dimethylchroman-4-yl)-N-methyl-methanesulfonamide (Example 2) and 2.1 g (13.8 mmol) of DBU in 4.2 ml of toluene was heated at 105° C. for 5 h. The reaction mixture was diluted with EA and washed with hydrochloric acid until the aqueous phase gave an acidic reaction. The mixture was washed with sodium bicarbonate solution, dried over magnesium sulfate and concentrated i. vac., giving 0.85 g of N-(6-benzyloxy-2,2-dimethyl-2H-chromen-4-yl)-N-methyl-methanesulfonamide.

Workup

  1. washwashed with hydrochloric acid until the aqueous phase
  2. customgave
  3. customan acidic reaction
  4. washThe mixture was washed with sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated i

Sources & evidence

ORD record
ord-77ffacc47bd54b4983c6b6118384e64e
Source dataset
uspto-grants-1999_12
Patent number
US06008245

Reaction notes

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