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Methyl iodide → 2-Adamantan-1-ylmethyl-1-methyl-5-phenyl-1h-pyrrole-3-carboxylic acid ethyl ester

HRID 1018305
ノート
印刷プレビュー

反応式

HRID 1018305 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:8][C:7]=1[CH2:17][C:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2)=[O:5])[CH3:2].[H-].[Na+].I[CH3:31]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([CH3:31])[C:7]=1[CH2:17][C:18]12[CH2:27][CH:22]3[CH2:21][CH:20]([CH2:26][CH:24]([CH2:23]3)[CH2:25]1)[CH2:19]2)=[O:5])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 117175262-Adamantan-1-ylmethyl-5-phenyl-1h-pyrrole-3-carboxylic acid ethyl ester

生成物 1

HCID 701183052-Adamantan-1-ylmethyl-1-methyl-5-phenyl-1h-pyrrole-3-carboxylic acid ethyl ester収率 82.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-adamantan-1-ylmethyl-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester (Example 1, step b) (726 mg, 2.00 mmol) in DMF (3 ml) was added sodium hydride (60% dispersion in oil) (100 mg, 2.50 mmol) in small portions at 0° C. The mixture was stirred at room temperature for 30 min, then iodomethane (1.00 ml, 16.0 mmol) was added and the stirring was continued for 1 h. The reaction mixture was partitioned between ethyl acetate and 1M hydrochloric acid, the organic layer was washed with water, dried, and the solvent was evaporated to afford the product as a white solid (620 mg, 82%). 1H NMR (300 MHz, CDCl3) 7.35 (5H, m), 6.64 (1H, s), 4.27 (2H, q), 3.51 (3H, s), 2.80 (2H, br s), 1.96 (3H, br s), 1.64 (12H, m), 1.35 (3H, t).

後処理

  1. waitthe stirring was continued for 1 h
  2. customThe reaction mixture was partitioned between ethyl acetate and 1M hydrochloric acid
  3. washthe organic layer was washed with water
  4. customdried
  5. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-4e4d0dcb8dce4745a380b4d5a671e958
出典データセット
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06479531B1

反応ノート

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