1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → HCID 23139275, compound

HRID 1171652Notes

Reaction equation

HRID 1171652 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](/[CH:17]=[C:18]2\[CH2:19][N:20]([CH:25]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[F:37])[C:26]([CH:28]3[CH2:30][CH2:29]3)=[O:27])[CH2:21][CH2:22][CH:23]\2O)=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:38]([OH:41])(=[S:40])[CH3:39].C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:38]([S:40][CH:23]1[CH2:22][CH2:21][N:20]([CH:25]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])[C:26]([CH:28]2[CH2:30][CH2:29]2)=[O:27])[CH2:19]/[C:18]/1=[CH:17]\[C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:9]=1)(=[O:41])[CH3:39]

Participants

6

Reactant 4

HCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 516892Sodium BicarbonateHCID 68766702HCID 68766702, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 23139275HCID 23139275, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (E)-3-{[1-(t-butoxycarbonyl)indol-3-yl]methylidene}-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]piperidin-4-ol (1.58 g) in toluene (32 ml) were added thioacetic acid (0.45 ml) and N,N-dimethylformamide dineopentyl acetal (1.75 ml) under ice-cooling, and the resulting mixture was stirred at room temperature for 1 hour. After stirring, to the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, 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 evaporated in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:9) as the eluent to afford (E)-4-(acetylsulfanyl)-3-{[1-(t-butoxycarbonyl)indol-3-yl]methylidene}-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]piperidine (0.66 g, yield: 38%) as a pale yellow amorphous solid.

Workup

  1. temperaturecooling
  2. stirringAfter stirring, to the reaction mixture
  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 evaporated in vacuo
  7. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-556fcf7ac9784c5a8a36929f499ebee1
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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