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Trifluoroacetic acid → methyl (3R*,4S*)-1-benzyl-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate

HRID 2047438
ノート
印刷プレビュー

反応式

HRID 2047438 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[Cl:14])[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[O:8].CO[CH2:17][N:18]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:19][Si](C)(C)C.FC(F)(F)C(O)=O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:24]([N:18]1[CH2:19][C@H:5]([C:4]2[CH:11]=[CH:12][C:13]([Cl:14])=[C:2]([Cl:1])[CH:3]=2)[C@@H:6]([C:7]([O:9][CH3:10])=[O:8])[CH2:17]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 54151376Methyl 3-(3,4-dichlorophenyl)prop-2-enoate

生成物 1

HCID 67232866methyl (3R*,4S*)-1-benzyl-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate収率 103.9%

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒
2 回

実験手順

To a solution of the compound (20.4 g) obtained in step 1 and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (22.0 g) in toluene (180 mL) was added a solution of trifluoroacetic acid (1.31 mL) in toluene (18 mL) at 0° C., and the mixture was stirred at room temperature for 14 hr. To the reaction solution was added ethyl acetate (300 mL), and the mixture was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10→25% ethyl acetate/hexane) to give methyl (3R*,4S*)-1-benzyl-4-(3,4-dichlorophenyl)pyrrolidine-3-carboxylate (33.4 g, 100%) as a pale-yellow oil.

後処理

  1. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  2. customdried
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10→25% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-02e2525ad34c485c847aba329ddbc476
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08592454B2

反応ノート

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