Imidazole → HCID 66700614, compound

HRID 1253729Notes

Reaction equation

HRID 1253729 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].CS(O[CH:13]1[CH2:30][CH2:29][C:16]2([CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH2:15][CH2:14]1)(=O)=O>CN(C=O)C.O>[N:1]1([CH:13]2[CH2:30][CH2:29][C:16]3([CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:20][CH2:21]3)[CH2:15][CH2:14]2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 86645838HCID 86645838, compound

Product 1

HCID 66700614HCID 66700614, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Imidazole (1.17 g, 17.3 mmol, 3.0 eq.) was added to a stirred suspension of NaH (20.16 mmol, 3.5 eq.) in DMF (10 ml) at 0° C. and the reaction mixture was allowed to stir at the same temperature for 20 min. A solution of tert-butyl 9-(methylsulfonyloxy)-3-azaspiro[5.5]undecane-3-carboxylate (2.0 g, 5.76 mmol, 1.0 eq.) in DMF (5 ml) was added to the reaction mixture at 0° C. and it was stirred at RT for 16 h. The reaction mixture was diluted with water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine (60 ml) and dried over sodium sulfate. The solvent was evaporated under reduced pressure to obtain the crude product which was purified by column chromatography (silica gel; 3% MeOH/MC) to yield the desired product as a colorless oil. Yield: 59% (1.10 g, 3.45 mmol).

Workup

  1. stirringit was stirred at RT for 16 h
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washThe combined organic layers were washed with brine (60 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customto obtain the crude product which
  7. customwas purified by column chromatography (silica gel; 3% MeOH/MC)

Sources & evidence

ORD record
ord-f43d4e94a6cc417d8968b33464350f5f
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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