Beta-Alanine → Diisopropyl Ether

HRID 280692Notes

Reaction equation

HRID 280692 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:14]3[CH2:15][CH2:16][CH:10]2[CH2:11][C:12](=O)[CH2:13]3)=[CH:5][CH:4]=1.[CH2:18]([O:20][C:21](=[O:25])[CH2:22][C:23]#[N:24])[CH3:19].N1[CH2:31][CH2:30][CH2:29]CC1.NCCC(O)=O>CN(C)C=O.CCOCC>[C:23]([C:22](=[C:13]1[CH2:12][CH2:11][CH:10]2[N:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:14]1[CH2:15][CH2:16]2)[C:21]([O:20][CH2:18][CH3:19])=[O:25])#[N:24].[CH:3]([O:2][CH:30]([CH3:29])[CH3:31])([CH3:8])[CH3:4]

Participants

8

Reactant 4

HCID 239Beta-AlanineHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 189196618-(4-Methoxyphenyl)-8-azabicyclo[3.2.1]octan-3-one

Product 2

HCID 7914Diisopropyl EtherHCID 54533282HCID 54533282, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

3.0 g of 8-(4-methoxyphenyl)-8-azabicyclo[3.2.1]octan-3-one were dissolved in 6 ml of dimethylformamide and treated with 1.8 ml of cyanoacetic acid ethyl ester, 0.2 ml of piperidine and 58 mg of β-alanine. The mixture was heated to 50° for 28 hours while stirring. After cooling to room temperature, the mixture was diluted with ether, washed four times with water, dried over sodium sulfate and concentrated under reduced pressure. Chromatography of the residue on 250 g of silica gel with hexane/ethyl acetate (3:2) yielded ethyl cyano-[8-(4-methoxyphenyl)-8-azabicyclo[3.2.1]octanylidene]acetate as a white solid, melting point 121°-122° (from isopropyl ether).

Workup

  1. temperatureThe mixture was heated to 50° for 28 hours
  2. washwashed four times with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-37b6ea8742744aeaadfab1960a89a7a7
Source dataset
uspto-grants-1986_05
Patent number
US04590270

Reaction notes

Loading…