Trifluoroacetic acid → (3S,4S)-1-Benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic Acid Ethyl Ester

HRID 1163350ノート

反応式

HRID 1163350 の反応式
[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[CH:6][CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH3:2].C(O[CH2:23][N:24]([CH2:32][Si](C)(C)C)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)CCCC.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4]([C@H:5]1[C@@H:6]([CH2:7][NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:32][N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:23]1)=[O:16])[CH3:2]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 5463862-Butenoic acid, 4-[[(1,1-dimethylethoxy)carbonyl]amino]-, ethyl esterHCID 10902461N-[(pentyloxy)methyl]-N-[(trimethylsilyl)-methyl]-benzenemethanamine

生成物 1

HCID 68420071(3S,4S)-1-Benzyl-4-(tert-butoxycarbonylamino-methyl)-pyrrolidine-3-carboxylic Acid Ethyl Ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2 g of 4-tert-butoxycarbonylamino-but-2-enoic acid ethyl ester (8.72 mmol) and 5.12 g N-[(pentyloxy)methyl]-N-[(trimethylsilyl)methyl]-benzene-methanamine (17.4 mmol) in 50 ml dichloromethane was added 10 micro-l. trifluoroacetic acid. The reaction was monitored by TLC. The reaction was complete after 10 min. The mixture was diluted with dichloromethane, washed with sat. sodium bicarbonate solution and brine, dried over Mg sulfate, filtered and the filtrate evaporated. The residue was purified by filtration over a short silica column, using a 7/3 hexane/ethyl acetate mixture as eluent.

後処理

  1. washwashed with sat. sodium bicarbonate solution and brine
  2. dry with materialdried over Mg sulfate
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. filtrationThe residue was purified by filtration over a short silica column

出典と根拠

ORDレコード
ord-4326f11222d64a129b129976b683fa56
出典データセット
uspto-grants-2010_10
特許番号
US07820823B2

反応ノート

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