Aluminium lithium hydride → 1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-amine

HRID 526174ノート

反応式

HRID 526174 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N+:7]([C:10]1[CH:11]=[N:12][N:13]([CH:15]2[CH2:20][CH2:19][N:18]([C:21](OC(C)(C)C)=O)[CH2:17][CH2:16]2)[CH:14]=1)([O-])=O>C1COCC1>[CH3:21][N:18]1[CH2:17][CH2:16][CH:15]([N:13]2[CH:14]=[C:10]([NH2:7])[CH:11]=[N:12]2)[CH2:20][CH2:19]1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 56777238tert-butyl 4-(4-nitro-1H-pyrazol-1-yl)piperidine-1-carboxylate

生成物 1

HCID 533023461-(1-methylpiperidin-4-yl)-1H-pyrazol-4-amine収率 91.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
60 °C

実験手順

To a suspension of lithium aluminum hydride (0.32 g, 8.4 mmol) in THF (15 mL) was added a solution of tert-butyl 4-(4-nitro-1H-pyrazol-1-yl)piperidine-1-carboxylate (500 mg, 1.7 mmol) in THF (10 mL) and the reaction mixture was stirred with heat at 60° C. for 16 h. The reaction mixture was cooled to 0° C. and quenched by the slow addition of ethanol (0.3 mL) then water (0.3 mL) and finally 3 N NaOH aq. (0.3 mL). The resulting mixture was stirred for 30 min, filtered and the filtrate was concentrated and dried to obtain the desired product (280 mg) which was used without any purification: ESI MS m/z 181 [M+H]+.

後処理

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched by the slow addition of ethanol (0.3 mL)
  3. stirringThe resulting mixture was stirred for 30 min
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customdried

出典と根拠

ORDレコード
ord-6fa2f75eb3564fd6ba72fb469b5bf7ce
出典データセット
uspto-grants-2016_05
特許番号
US09345709B2

反応ノート

読み込み中…