Methyl iodide → 2-[Methyl-(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester

HRID 1047761ノート

反応式

HRID 1047761 の反応式
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1([NH:17][C:18]([C:20]2[C:29]3[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=3[CH:23]=[CH:22][CH:21]=2)=[O:19])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])[CH3:4].[CH3:30]I>C1COCC1>[CH2:3]([O:5][C:6]([C:8]1([N:17]([CH3:30])[C:18]([C:20]2[C:29]3[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=3[CH:23]=[CH:22][CH:21]=2)=[O:19])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])[CH3:4]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 593141592-[(5,6,7,8-Tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester

生成物 1

HCID 593141972-[Methyl-(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester収率 86%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of NaH (sodium hydride, 60% dispersion, 124 mg, 3.08 mmol) in anhydrous THF (20 mL) is added dropwise the solution of 2-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (37) (280 mg, 0.77 mmol) in THF (5 mL) at 0° C. After stirring for 20 min, methyl iodide (377 μL, 6.05 mmol) is added dropwise and the resulting suspension is warmed up to RT and continued stirring overnight. After being quenched by saturated ammonium chloride aqueous solution (5 mL), the reaction mixture is diluted in EtOAc (50 mL). The organic layer is separated, washed with water (1×5 mL) and brine (2×5 mL), dried over anhydrous Na2SO4 and concentrated in in vacuo. The residue is purified by flash column chromatography (115 g silica gel, gradient elution: 0%-30% EtOAc in heptane) to give a pure product (120) as a colorless semisolid (250 mg, 86%).

後処理

  1. stirringcontinued stirring overnight
  2. customAfter being quenched by saturated ammonium chloride aqueous solution (5 mL)
  3. additionthe reaction mixture is diluted in EtOAc (50 mL)
  4. customThe organic layer is separated
  5. washwashed with water (1×5 mL) and brine (2×5 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in in vacuo
  8. customThe residue is purified by flash column chromatography (115 g silica gel, gradient elution: 0%-30% EtOAc in heptane)

出典と根拠

ORDレコード
ord-6d0db7c7a9704ccab19f3298a7a0185f
出典データセット
uspto-grants-2013_10
特許番号
US08569535B2

反応ノート

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