Water → HCID 69196212, compound

HRID 1594160Notes

Reaction equation

HRID 1594160 reaction equation
[CH2:1]1[C:3]2([CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]2[CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[NH:18][C:17]3=[O:25])[CH2:12][CH2:11]2)[CH2:2]1.[H-].[Na+].CC1C=CC(S(O[CH2:39][C@@H:40]2[CH2:44][O:43][C:42]([CH3:46])([CH3:45])[O:41]2)(=O)=O)=CC=1.O>CN(C)C=O>[CH3:45][C:42]1([CH3:46])[O:41][C@H:40]([CH2:39][N:18]2[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:16]([CH:13]3[CH2:12][CH2:11][N:10]([CH2:9][C@H:4]4[CH2:5][CH2:6][CH2:7][CH2:8][C:3]54[CH2:2][CH2:1]5)[CH2:15][CH2:14]3)[C:17]2=[O:25])[CH2:44][O:43]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2723760(S)-(+)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-ToluenesulfonateHCID 68622797HCID 68622797, compound

Product 1

HCID 69196212HCID 69196212, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-{1-[(4S)-spiro[2.5]oct-4-ylmethyl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one (2.94 g) was dissolved in dimethylformamide (60 mL), and to which 60-72% sodium hydride (oil dispersion) (706.6 mg) was added at room temperature and stirred for 30 minutes. To the reaction mixture, [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzene-sulfonate (7.25 g) was added and stirred at 80° C. for 7 hours. After cooling the reaction mixture to room temperature, water was added, followed by extraction with ethyl acetate. The extract washed with saturated brine, dried over anhydrous magnesium sulfate, the solvent was removed by distillation and the resulting residue was purified on silica gel column chromatography (hexane/ethyl acetate=2/1−1/2) to provide 3.43 g of the title compound as a pale yellow, oily substance.

Workup

  1. stirringstirred at 80° C. for 7 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation
  6. customthe resulting residue was purified on silica gel column chromatography (hexane/ethyl acetate=2/1−1/2)

Sources & evidence

ORD record
ord-85bd6cb4b2df4a8ba1356d9de99e36f0
Source dataset
uspto-grants-2007_11
Patent number
US07300947B2

Reaction notes

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