2,6-Lutidine → 5-(Tert-butyl-dimethyl-silanyloxy)-3-methyl-1h-pyrrole-2-carboxylic acid methyl ester

HRID 639867ノート

反応式

HRID 639867 の反応式
[Si:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:16][O:17][C:18]([CH:20]1[C:24]([CH3:25])=[CH:23][C:22](=O)[N:21]1C(OC(C)(C)C)=O)=[O:19].N1C(C)=CC=CC=1C>ClCCl>[CH3:16][O:17][C:18]([C:20]1[NH:21][C:22]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:23][C:24]=1[CH3:25])=[O:19]

参加物

5

反応物 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 575874573-Methyl-5-oxo-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

生成物 1

HCID 575874385-(Tert-butyl-dimethyl-silanyloxy)-3-methyl-1h-pyrrole-2-carboxylic acid methyl ester収率 89%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
23 °C

実験手順

tert-Butyldimethylsilyltrifluoromethanesulfonate (9.99 ml, 11.49 g, 43.5 mmol, 3.0 equiv) was added to a stirring solution of 3-methyl-5-oxo-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (3.7 g, 14.5 mmol, 1.0 equiv) and 2,6-lutidine (5.07 ml, 4.66 g, 43.5 mmol, 3.0 equiv) in dichloromethane (100 ml) at 23° C. The mixture was stirred at 23° C. for 15 h, then washed with pH=7 buffer solution (30 ml). The aqueous layer was extracted with two 40 ml portions of dichloromethane. The combined organic layers were dried over sodium sulfate. The solids were filtered and the filtrate was concentrated. The residue was purified by flash column chromatography (3% ethyl acetate-hexanes initially, grading to 6% ethyl acetate-hexanes) to afford 5-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-1H-pyrrole-2-carboxylic acid methyl ester (3.46 g, 89%) as a yellow oil.

後処理

  1. washwashed with pH=7 buffer solution (30 ml)
  2. extractionThe aqueous layer was extracted with two 40 ml portions of dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationThe solids were filtered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash column chromatography (3% ethyl acetate-hexanes initially

出典と根拠

ORDレコード
ord-0fdd89974f2640a0a6d1785b7ce98db8
出典データセット
uspto-grants-2010_04
特許番号
US07691896B2

反応ノート

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