N-bromobutanimide → Tert-butyl 2-{2-[6-bromo-3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenyl]-ethyl}-pyrrolidine-1-carboxylate

HRID 715970ノート

反応式

HRID 715970 の反応式
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]([CH3:39])([CH3:38])[C:11]([NH:13][C:14]1[C:15]([C:34]([O:36][CH3:37])=[O:35])=[C:16]([CH2:20][CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][N:23]2[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:17]=[CH:18][CH:19]=1)=[O:12]>C(#N)C>[Br:1][C:17]1[C:16]([CH2:20][CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][N:23]2[C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])=[C:15]([C:34]([O:36][CH3:37])=[O:35])[C:14]([NH:13][C:11](=[O:12])[C:10]([CH3:39])([CH3:38])[CH3:9])=[CH:19][CH:18]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 70984356Tert-butyl 2-{2-[3-(2,2-dimethylpropionylamino)-2-methoxycarbonyl-phenyl]-ethyl}-pyrrolidine-1-carboxylate2 回

生成物 1

HCID 70982387Tert-butyl 2-{2-[6-bromo-3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenyl]-ethyl}-pyrrolidine-1-carboxylate収率 78.7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

N-Bromosuccinimide (1.24 g) was added to a solution of tert butyl 2-{2-[3-(2,2-dimethyl-propionylamino)-2-methoxycarbonylphenyl]-ethyl}-pyrrolidine-1-carboxylate (Intermediate 37, 2.74 g) in acetonitrile (40 mL) and the resultant mixture was stirred for 1 hour at room temperature. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was dried (Na2SO4) and filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-25% to give tert butyl 2-{2-[6-bromo-3-(2,2-dimethylpropionylamino)-2-methoxycarbonylphenyl]-ethyl}-pyrrolidine-1-carboxylate (2.55 g) as a colourless gum.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by chromatography on silica
  7. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-25%

出典と根拠

ORDレコード
ord-2a727defd0414013b3aa24abdc6a35c3
出典データセット
uspto-grants-2015_11
特許番号
US09187494B2

反応ノート

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