Methyl iodide → 2,3-dihydro-2-methyl-7-methoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-pyrrolo[1,2-a]indol-1-one

HRID 22287ノート

反応式

HRID 22287 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]3[CH2:12][CH:13]([CH2:16][CH:17]4[CH2:22][CH2:21][N:20]([CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:19][CH2:18]4)[C:14](=[O:15])[C:7]3=[CH:6][C:5]=2[CH:4]=1.[H-].[Na+].[CH3:32]I>C1COCC1>[CH3:32][C:13]1([CH2:16][CH:17]2[CH2:18][CH2:19][N:20]([CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:21][CH2:22]2)[CH2:12][N:8]2[C:9]3[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH:6]=[C:7]2[C:14]1=[O:15]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 538715712,3-dihydro-7-methoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-pyrrolo[1,2-a]indol-1-one

生成物 1

HCID 199278542,3-dihydro-2-methyl-7-methoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-pyrrolo[1,2-a]indol-1-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 2,3-dihydro-7-methoxy-2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-pyrrolo[1,2-a]indol-1-one (137 mg, 0.353 mmol) in dry THF (5 ml) was treated with NaH (35 mg, 0.875 mmol) at r.t. After 5 minutes, an excess of methyl iodide (0.1 ml) was added and the mixture was stirred at r.t. for 3 hours. The mixture was quenched with water and extracted with chloroform. The organic layer was dried and concentrated to give 140 mg of material which was purified through silica gel to give the title compound. 1HNMR (CDCl3)δ 1.36 (s, 3H), 1.6-2.2 (m, 7H), 2.4-2.7 (m, 2H), 3.2-3.4 (m, 2H), 3.8 (s, 3H), 4.05 (s, 2H), 4.18 (ABq, 2H), 6.9 (s, 1H), 7.0-7.1 (m, 2H), 7.2-7.3 (m, 1H), 7.3-7.4 (m, 3H), 7.4-7.6 (m, 2H) ppm.

後処理

  1. customThe mixture was quenched with water
  2. extractionextracted with chloroform
  3. customThe organic layer was dried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-5d4c8e44a481482486c8f0185c650681
出典データセット
uspto-grants-1995_06
特許番号
US05428043

反応ノート

読み込み中…