Ethyl Acetate → (+/-)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile

HRID 1432803ノート

反応式

HRID 1432803 の反応式
[CH3:1][C:2]1([CH3:14])[CH:4]2[CH2:5][C:6]3[C:10]([CH:3]12)=[N:9][NH:8][C:7]=3[C:11]([NH2:13])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OCC)(=O)C>C1COCC1>[CH3:1][C:2]1([CH3:14])[CH:4]2[CH2:5][C:6]3[C:10]([CH:3]12)=[N:9][NH:8][C:7]=3[C:11]#[N:13]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 9845Trifluoroacetic anhydrideHCID 178421816HCID 178421816、化合物

生成物 1

HCID 178421815(+/-)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(±)-1,1-Dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid amide (0.532 g, 2.79 mmol) was taken up in THF (150 mL) and trifluoroacetic anhydride (0.936 g, 4.46 mmol) added. The resulting solution was stirred at room temperature under argon for 1 hour. Ethyl acetate (50 mL) was added and solvent removed under reduced pressure. The resulting pale yellow oil was taken up in DCM (100 mL), washed with saturated aqueous sodium bicarbonate solution (40 mL) and solvent removed under reduced pressure. The resulting white solid was taken up as a suspension in DCM (20 mL) and filtered to give (±)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile as an off-white solid. m/z (ES+): 174 [M+H]+

後処理

  1. customsolvent removed under reduced pressure
  2. washwashed with saturated aqueous sodium bicarbonate solution (40 mL) and solvent
  3. customremoved under reduced pressure
  4. filtrationfiltered

出典と根拠

ORDレコード
ord-06a73ddfeaa24553acba18095d3489af
出典データセット
uspto-grants-2009_11
特許番号
US07612106B2

反応ノート

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