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Benzenesulfonyl chloride → (R)-3-(1-methyl-2-pyrrolidinylmethyl)-1-phenylsulfonylindole

HRID 1870966
ノート
印刷プレビュー

反応式

HRID 1870966 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][N:12]1[CH2:16][CH2:15][CH2:14][C@@H:13]1[CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1.[C:27]1([S:33](Cl)(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[CH3:11][N:12]1[CH2:16][CH2:15][CH2:14][C@@H:13]1[CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([S:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:35])=[O:34])[CH:19]=1
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 7369Benzenesulfonyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 44397420(R)-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole

生成物 1

HCID 11624561(R)-3-(1-methyl-2-pyrrolidinylmethyl)-1-phenylsulfonylindole収率 46.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium bis(trimethylsilyl)amide (0.25 mL, 1M in THF, 0.25 mmol) was added to a solution of (R)-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indole (Example 3e, 25.8 mg, 0.12 mmol) in THF (1.5 mL) at -78° C. and the mixture was stirred for 1 h. Phenylsulfonyl chloride (50 μL, 0.39 mmol) was added and the mixture stirred at room temperature for 1 h. prior to quenching with water (6 drops) and silica gel (~1 g). Purification using solid phase extraction tubes (1000 mg silica) eluting with 2M methanolic ammonia in dichloromethane (0-4%) yielded (R)-3-(1-methyl-2-pyrrolidinylmethyl)-1-phenylsulfonylindole (19.7 mg, 46%, HRMS-FAB+ for C20H22N2O2S: calculated MH+ :355.14801; found MH+ :355.14837).

後処理

  1. stirringthe mixture stirred at room temperature for 1 h.
  2. customto quenching with water (6 drops) and silica gel (~1 g)
  3. customPurification
  4. extractionsolid phase extraction tubes (1000 mg silica)
  5. washeluting with 2M methanolic ammonia in dichloromethane (0-4%)

出典と根拠

ORDレコード
ord-69dcccc4e40a4525850274015f534ac2
出典データセット
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06100291

反応ノート

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