Methanol → benzyl 3-[1-(2-aminoethyl)-7-bromo-3-methyl-1H-indol-6-ylmethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1712358

反応式

HRID 1712358 の反応式
[Br:1][C:2]1[C:3]([CH2:15][O:16][CH:17]2[CH:22]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[O:41][CH3:42])=[CH:25][CH:24]=3)[CH2:21][CH2:20][N:19]([C:43]([O:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[O:44])[CH2:18]2)=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][C:12]#[N:13])[CH:8]=[C:7]2[CH3:14].B#B.CO>O1CCCC1>[NH2:13][CH2:12][CH2:11][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([CH2:15][O:16][CH:17]3[CH:22]([C:23]4[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=5[O:41][CH3:42])=[CH:27][CH:28]=4)[CH2:21][CH2:20][N:19]([C:43]([O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[O:44])[CH2:18]3)[C:2]=2[Br:1])[C:7]([CH3:14])=[CH:8]1

参加物

5

反応物 3

HCID 887MethanolHCID 6328200DiboronHCID 68501271benzyl 3-(7-bromo-1-cyanomethyl-3-methyl-1H-indol-6-ylmethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

生成物 1

HCID 68504218benzyl 3-[1-(2-aminoethyl)-7-bromo-3-methyl-1H-indol-6-ylmethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The solution of 0.240 g of benzyl 3-(7-bromo-1-cyanomethyl-3-methyl-1H-indol-6-ylmethoxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 1.5 ml of tetrahydrofuran is cooled to 0° C. with stirring and admixed with 1.22 ml of diborane (1M in tetrahydrofuran). The reaction mixture is stirred at 0° C. over 1 hour and subsequently admixed cautiously with 1.0 ml of methanol and concentrated by evaporation. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.46 (200:20:1 dichloromethane-methanol-conc. ammonia); Rt=5.45.

後処理

  1. stirringThe reaction mixture is stirred at 0° C. over 1 hour
  2. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-dab2e6c0f1894475bb3e043cf961d06e
出典データセット
uspto-grants-2010_09
特許番号
US07790715B2

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