4-Toluenesulfonyl chloride → 2-Nitro-4-pyrrolidin-1-ylmethyl-benzoic acid methyl ester

HRID 1921086ノート

反応式

HRID 1921086 の反応式
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]O)=[CH:6][C:5]=1[N+:12]([O-:14])=[O:13].[CH2:16]([N:18](CC)[CH2:19][CH3:20])[CH3:17].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.N1CCCC1>ClCCl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:18]2[CH2:19][CH2:20][CH2:17][CH2:16]2)=[CH:6][C:5]=1[N+:12]([O-:14])=[O:13]

参加物

6

反応物 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 31268PyrrolidineHCID 22672700Methyl 4-(hydroxymethyl)-2-nitrobenzoate

生成物 1

HCID 574473262-Nitro-4-pyrrolidin-1-ylmethyl-benzoic acid methyl ester収率 44.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-hydroxymethyl-2-nitro-benzoic acid methyl ester (2.0 g, 9.47 mmol) in dry dichloromethane (80 mL) under argon, at room temperature, triethylamine (1.6 mL, 10.9 mmol, 1.15 eq.) and then p-toluenesulfonyl chloride (2.08 g, 10.9 mmol, 1.15 eq.) were added. The reaction mixture was stirred at room temperature for 1 h, then pyrrolidine (1.6 mL, 18.94 mmol, 2 eq.) was added and the mixture stirred for additional 24 hours. The solvent was evaporated and the residue purified by flash chromatography on silica gel, using dichloromethane-ethanol 95:5 as eluant, affording the title compound (1.12 g).

後処理

  1. stirringthe mixture stirred for additional 24 hours
  2. customThe solvent was evaporated
  3. customthe residue purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-9a25f8d7a84b43b49d86bb7546bb1447
出典データセット
uspto-grants-2012_05
特許番号
US08173659B2

反応ノート

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