1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → HCID 86609407, compound

HRID 1171639Notes

Reaction equation

HRID 1171639 reaction equation
[CH:1]1([C:4](=[O:26])[CH:5]([N:13]2[CH2:18][CH2:17][CH:16](O)/[C:15](=[CH:20]/[C:21]3[O:22][CH:23]=[CH:24][CH:25]=3)/[CH2:14]2)[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[F:12])[CH2:3][CH2:2]1.[C:27]([OH:30])(=[S:29])[CH3:28].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:27]([S:29][CH:16]1[CH2:17][CH2:18][N:13]([CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[F:12])[C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:26])[CH2:14]/[C:15]/1=[CH:20]\[C:21]1[O:22][CH:23]=[CH:24][CH:25]=1)(=[O:30])[CH3:28]

Participants

6

Reactant 4

HCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 516892Sodium BicarbonateHCID 23138736HCID 23138736, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86609407HCID 86609407, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (E)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-[(furan-2-yl)methylidene]piperidin-4-ol (2.30 g) in toluene (50 ml) were added thioacetic acid (0.92 ml) and N,N-dimethylformamide dineopentyl acetal (3.61 g) under ice-cooling, and the resulting mixture was stirred at room temperature for 1 hour. After stirring, saturated aqueous sodium hydrogencarbonate solution 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 1:9) as the eluent to afford the title compound (0.58 g, yield: 22%) as an orange-coloured oil.

Workup

  1. temperaturecooling
  2. stirringAfter stirring
  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-ffa9e718b02143efa45475046b225ebe
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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