Water → HCID 86609424, compound

HRID 1171666Notes

Reaction equation

HRID 1171666 reaction equation
[CH3:1][O:2][C:3]([CH2:5][N:6]1[CH:10]=[CH:9][C:8](/[CH:11]=[C:12]2\[CH2:13][N:14]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:16][CH:17]\2O)=[CH:7]1)=[O:4].[C:38]([OH:41])(=[S:40])[CH3:39].C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.O>C1(C)C=CC=CC=1.CO>[C:38]([S:40][CH:17]1[CH2:16][CH2:15][N:14]([C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:13]/[C:12]/1=[CH:11]\[C:8]1[CH:9]=[CH:10][N:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH:7]=1)(=[O:41])[CH3:39]

Participants

7

Reactant 4

HCID 962WaterHCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 23138721HCID 23138721, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86609424HCID 86609424, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of (E)-3-{[1-(methoxycarbonylmethyl)pyrrol-3-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol (12.1 g) in toluene (100 ml) were added thioacetic acid (3.5 ml) and N,N-dimethylformamide dineopentyl acetal (13.7 ml) under ice-cooling, and the resulting mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added water, 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 magnesium 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 (1:3) as the eluent. The amorphous solid obtained was dissolved in methanol (100 ml), and the resulting mixture was stirred at 50° C. for 2 days. The reaction mixture was concentrated in vacuo to afford the title compound (12.8 g, yield: 95%) as a pale yellow amorphous solid.

Workup

  1. temperaturecooling
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by chromatography on a silica gel column
  7. customThe amorphous solid obtained
  8. stirringthe resulting mixture was stirred at 50° C. for 2 days
  9. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-ed9b9820f13d4c9ca6c91b326e5375fe
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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