Hydroxide → (R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

HRID 745002ノート

反応式

HRID 745002 の反応式
C([N:8](CC1C=CC=CC=1)[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][C@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH3:24])C1C=CC=CC=1.[OH-]>C(O)C.[Pd]>[NH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:18][C@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH3:24]

参加物

5

反応物 2

HCID 961HydroxideHCID 10364175(R)-5-dibenzylamino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

生成物 1

HCID 10376533(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole収率 99.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
40 °C

実験手順

A mixture of (R)-5-dibenzylamino-3-(N-methylpyrrolidin-2-ylmethyl)indole (1.08 g, 2.64 mmol) and palladium [II] hydroxide on carbon (0.6 g) in absolute ethanol (25 mL) was shaken under a hydrogen atmoshpere (3 atm) at 40° C. for 4 hours. The resulting mixture was filtered through diatomaceous earth, and the filtrate was evaporated under pressure to afford the title compound (0.60 g, 2.62 mmol, 99%) as a white foam: 1H NMR (DMSO-d6) δ 10.65 (br s, NH), 7.14 (d, J=2.2 Hz, 1H), 7.12 (d, J=8.6 Hz, 1H), 6.85 (d, J=1.6 Hz, 1H), 6.60 (dd, J=2.0 and 8.6 Hz, 1H), 3.63-2.83 (m, 7H), 2.78 (s, 3H), 2.05-1.67 (m, 4H); [α]25D =+9° (MeOH, c=1.0); HRMS: calculated for C14H19N3 : 229.1575; found 229.1593.

後処理

  1. filtrationThe resulting mixture was filtered through diatomaceous earth
  2. customthe filtrate was evaporated under pressure

出典と根拠

ORDレコード
ord-235b837457dd439faef92b46cd693a29
出典データセット
uspto-grants-1996_09
特許番号
US05559246

反応ノート

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