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

HRID 1263435노트

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HRID 1263435 반응식
[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

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 105390775-(Azidomethyl)-1-(2-tetrahydropyranyl)indazole2회HCID 21226445Aluminium lithium hydride

생성물 1

HCID 108234185-(Aminomethyl)-1-(2-tetrahydropyranyl)indazole수율 92%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c401f4100e1347e190f3b89154f0a616
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06541467B1

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