Ammonium Chloride → tert-Butyl N-[(3S)-1-(4-bromo-3-methylphenyl)-5-oxopyrrolidin-3-yl]carbamate

HRID 715924ノート

反応式

HRID 715924 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[CH3:9].[O:10]=[C:11]1[NH:15][CH2:14][C@@H:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12]1.[F-].[Cs+].CN(C)CCN.[Cl-].[NH4+]>C(#N)C.[Cu](I)I>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:15]2[C:11](=[O:10])[CH2:12][C@H:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:14]2)=[CH:4][C:3]=1[CH3:9]

参加物

8

反応物 5

HCID 25517Ammonium ChlorideHCID 25953Cesium fluorideHCID 66053N,N-DimethylethylenediamineHCID 27355742-Bromo-5-iodotolueneHCID 45091936(S)-tert-Butyl (5-oxopyrrolidin-3-yl)carbamate

生成物 1

HCID 117893476tert-Butyl N-[(3S)-1-(4-bromo-3-methylphenyl)-5-oxopyrrolidin-3-yl]carbamate収率 96.5%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

A suspension of 2-bromo-5-iodotoluene (1.5 g), tert-butyl ((S)-5-oxopyrrolidin-3-yl)carbamate (2.7 g), copper iodide (95 mg), cesium fluoride (1.9 g), and N,N-dimethylethylenediamine (0.11 ml) in acetonitrile (20 ml) was stirred at 100° C. for 3 hours under a nitrogen atmosphere. After cooling, a saturated aqueous solution of ammonium chloride was added to the reaction solution, followed by extraction with ethyl acetate. The extract was washed with a 10% aqueous sodium thiosulfate solution and saturated saline in this order and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform-methanol) to obtain the title compound (1.8 g).

後処理

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with a 10% aqueous sodium thiosulfate solution and saturated saline in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform-methanol)

出典と根拠

ORDレコード
ord-33b112249b754d16a700070604b8e3d4
出典データセット
uspto-grants-2015_11
特許番号
US09187489B2

反応ノート

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