Sodium Bicarbonate → 3-Ethyl-5-[1-(4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one

HRID 515432ノート

反応式

HRID 515432 の反応式
[CH2:1]([N:3]1[N:7]=[C:6]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17](/[N:20]=[CH:21]/[C:22]4[O:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=4)=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[O:5][C:4]1=[O:30])[CH3:2].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CC(O)=O.CO>[CH2:1]([N:3]1[N:7]=[C:6]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]3[CH:15]=[CH:16][C:17]([NH:20][CH2:21][C:22]4[O:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=4)=[CH:18][CH:19]=3)[CH2:12][CH2:13]2)[O:5][C:4]1=[O:30])[CH3:2]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 178463007HCID 178463007、化合物

生成物 1

HCID 716170393-Ethyl-5-[1-(4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one収率 87%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 887Methanol溶媒

実験手順

3-Ethyl-5-[1-(4[(E)-1-(5-nitro-2-furyl)methylidene]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (9c, 0.41 g, 1 mmol) on reduction with sodiumcyano borohydride (0.12 g, 2 mmol) in the presence of catalytic amount of CH3COOH (3 drops) in methanol at 0° C. for 12 h. After completion of the reaction as indicated by TLC, the reaction mixture is neutralized with sodium bi carbonate and extracted into chloroform. The crude product thus obtained was purified by column chromatography using ethyl acetate-hexane (8:2) as eluant to obtain product 3-ethyl-5-[1-(4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (10c, 359 mg, 87%).

後処理

  1. customAfter completion of the reaction
  2. extractionextracted into chloroform
  3. customThe crude product thus obtained
  4. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-635d7a21041c4a76ac13040557ad8c69
出典データセット
uspto-grants-2015_08
特許番号
US09108960B2

反応ノート

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