Potassium hydride → N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-(4-phenylbutoxy)-2-propanamine

HRID 1734688ノート

反応式

HRID 1734688 の反応式
[C:1]([NH:20][CH:21]([CH2:40][OH:41])[CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[O:32][C:33]3[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=3[N:35]=2)=[CH:27][CH:26]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[K+].[C:44]1([CH2:50][CH2:51][CH2:52][CH2:53]I)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C1COCC1>[C:1]([NH:20][CH:21]([CH2:40][O:41][CH2:53][CH2:52][CH2:51][CH2:50][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:22][O:23][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]2[O:32][C:33]3[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=3[N:35]=2)=[CH:29][CH:30]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 82127Potassium hydrideHCID 12709818(4-Iodobutyl)benzeneHCID 19420787N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-hydroxy-2-propanamine

生成物 1

HCID 19420792N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-(4-phenylbutoxy)-2-propanamine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
20 °C

実験手順

N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-hydroxy-2-propanamine (0.4 g; 0.74 mmol) is added to a suspension of potassium hydride (0.12 g; 1. mmol; 35% suspension in oil) in dry THF (4 ml) at 0° C. The reaction is stirred for 15 minutes at 20° C. 4-Phenyl-1-butyl iodide (0.21 g; 0.81 mmol) is added and the reaction mixture stirred for 15 hours. The reaction is quenched with MeOH, diluted with CH2Cl2 and washed with water 2x. The organic phase is dried (Na2SO4), concentrated and purified by column chromatography with 80% CH2Cl2 /20% petroleum ether to yield N-trityl-1-[4-(benzoxazol-2-yl)benzyloxy]-3-(4-phenylbutoxy)-2-propanamine as an oil which is used directly in Step F.

後処理

  1. stirringthe reaction mixture stirred for 15 hours
  2. customThe reaction is quenched with MeOH
  3. additiondiluted with CH2Cl2
  4. washwashed with water 2x
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified by column chromatography with 80% CH2Cl2 /20% petroleum ether

出典と根拠

ORDレコード
ord-3800d536b0764b818291d1eb14bacd76
出典データセット
uspto-grants-1996_07
特許番号
US05534532

反応ノート

読み込み中…