Ethyl Acetate → 5-(Aminomethyl)-1-(2-tetrahydropyranyl)indazole

HRID 1263435ノート

反応式

HRID 1263435 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]([CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)[N:15]=[CH:14]2)=[N+]=[N-].[OH-].[Na+].C(OCC)(=O)C>C1COCC1>[NH2:7][CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][O:21]1)[N:15]=[CH:14]2

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 105390775-(Azidomethyl)-1-(2-tetrahydropyranyl)indazole2 回HCID 21226445Aluminium lithium hydride

生成物 1

HCID 108234185-(Aminomethyl)-1-(2-tetrahydropyranyl)indazole収率 92%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of LiAlH4 (Aldrich, 10.5 mL, 10.5 mmol, 1.0 M) in THF was added dropwise into a yellow solution of 5-(azidomethyl)-1-(2-tetrahydropyranyl)indazole (compound 94, 2.6 g, 10.1 mmol) in THF (30 mL) at 0° C. The addition time was 10 minutes and gas was released. After stirring at 0° C. for 1 hour, NaOH (1.0M, 1.5 mL) was added. The reaction mixture was allowed to warm to room temperature. Ethyl acetate (100 mL) was added, and the suspension was filtered (Celite). The filter cake was washed with an addition portion of ethyl acetate (40 mL). Combined organic layers were evaporated under vacuum to give free amine 63 (2.14 g, 92%). MS (electrospray) 232.5 (M+1); 1H NMR (CDCl3) δ1.61 (m, 3H), 2.02 (m, 2H), 2.50 (m, 1H), 2.83 (br s, 2H), 3.68 (m, 1H), 3.85 (s, 2H), 3.95 (m, 1H), 5.62 (d, 1H, J=9.2 Hz), 7.29 (d, 1H, J=8.8 Hz), 7.48 (d, 1H, J=8.8 Hz), 7.53 (s, 1H), 7.92 (s, 1H).

後処理

  1. temperatureto warm to room temperature
  2. filtrationthe suspension was filtered (Celite)
  3. washThe filter cake was washed with an addition portion of ethyl acetate (40 mL)
  4. customCombined organic layers were evaporated under vacuum

出典と根拠

ORDレコード
ord-c401f4100e1347e190f3b89154f0a616
出典データセット
uspto-grants-2003_04
特許番号
US06541467B1

反応ノート

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