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

HRID 1921086노트

반응식

HRID 1921086 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-9a25f8d7a84b43b49d86bb7546bb1447
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173659B2

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