Triethylamine → Tert-butyl 2-(3-(3-cyanophenyl)-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate

HRID 1791360ノート

反応式

HRID 1791360 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[C:32]([C:34]1[CH:35]=[C:36]([CH:41]=[CH:42][CH:43]=1)[C:37]([NH:39]O)=[NH:38])#[N:33]>C1COCC1.ClCCl.O.CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]1[O:16][N:39]=[C:37]([C:36]2[CH:41]=[CH:42][CH:43]=[C:34]([C:32]#[N:33])[CH:35]=2)[N:38]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

9

反応物 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 5818311-[(Tert-butoxy)carbonyl]piperidine-2-carboxylic acidHCID 178509779HCID 178509779、化合物

生成物 1

HCID 69619392Tert-butyl 2-(3-(3-cyanophenyl)-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate収率 98.5%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (5.32 g, 23.2 mmol) and triethylamine (4.04 g, 40 mmol) in THF (50 mL), isobutyl chloroformate (3.0 mL, 25.5 mmol) was added dropwise. After the mixture was stirred at room temperature for 45 min, 3-cyano-N-hydroxy-benzamidine (3.7 g, 23.2 mmol) and DMF (40 mL) were added. After being stirred for another hour, the reaction mixture was heated to 130˜135° C. for 1.5 h. Then the solution was cooled to room temperature and poured into water. Dichloromethane was used to extract the product. The organic layer was dried with sodium sulfate and concentrated in vacuo to give 8.1 g (98.4%) of the title compound as a thick brown oil.

後処理

  1. additionwas added dropwise
  2. stirringAfter being stirred for another hour
  3. temperaturethe reaction mixture was heated to 130˜135° C. for 1.5 h
  4. temperatureThen the solution was cooled to room temperature
  5. extractionto extract the product
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f98dd5e94fc24360a3b4c09c127afdb6
出典データセット
uspto-grants-2006_07
特許番号
US07074809B2

反応ノート

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