Water → HCID 68766704, compound

HRID 1171650Notes

Reaction equation

HRID 1171650 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11]/[C:10]/1=[CH:34]\[CH:35]=[O:36])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(C)C=CC(S([CH2:46][N+:47]#[C-:48])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CO>[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:11]/[C:10]/1=[CH:34]\[C:35]1[O:36][CH:48]=[N:47][CH:46]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 86609417HCID 86609417, compound

Product 1

HCID 68766704HCID 68766704, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (E)-4-(t-butyldimethylsilyloxy)-3-(formylmethylidene)-1-(triphenylmethyl)piperidine (112 mg) in methanol (2.5 ml) were added successively p-toluenesulfonylmethyl isocyanide (45 mg) and potassium carbonate (32 mg), and the resulting mixture was refluxed for 3.5 hours. After refluxing, water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:19 to 1:3) as the eluent to afford the title compound (40 mg, yield: 32%) as a yellow oil.

Workup

  1. temperaturethe resulting mixture was refluxed for 3.5 hours
  2. temperatureAfter refluxing
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-d42228b524304af58aba019f0404eee1
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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