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

HRID 515436ノート

反応式

HRID 515436 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][C:15]=3[F:30])[CH2:10][CH2:9]2)[O:5][C:4]1=[O:31])[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:19]=[CH:18][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:16][C:15]=3[F:30])[CH2:12][CH2:13]2)[O:5][C:4]1=[O:31])[CH3:2]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 178463008HCID 178463008、化合物

生成物 1

HCID 716170433-Ethyl-5-[1-(2-fluoro-4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-2,3-di hydro-1,3,4-oxadiazol-2-one収率 83%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 887Methanol溶媒

実験手順

3-Ethyl-5-[1-(2-fluoro-4-[(E)-1-(5-nitro-2-furyl)methylidene]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (9 g, 0.43 g, 1 mmol) on reduction with sodiumcyanoborohydride (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-(2-fluoro-4-[(5-nitro-2-furyl)methyl]aminophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadi azol-2-one (10g, 357 mg, 83%).

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-16287b7a877f475b9a495640abf428d3
出典データセット
uspto-grants-2015_08
特許番号
US09108960B2

反応ノート

読み込み中…