Ethyl Acetate → tert-butyl (RS)-3-(4-amino-3-chlorophenyl)pyrrolidine-1-carboxylate

HRID 571832ノート

反応式

HRID 571832 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Cl:27])C(=O)C1.CCOC(C)=O>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]2)=[CH:6][C:7]=1[Cl:27]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 573650691,1-Dimethylethyl 3-(4-aminophenyl)-1-pyrrolidinecarboxylate

生成物 1

HCID 86674689tert-butyl (RS)-3-(4-amino-3-chlorophenyl)pyrrolidine-1-carboxylate収率 51.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

To a stirred solution of tert-butyl 3-(4-aminophenyl)pyrrolidine-1-carboxylate (2.00 g, CAS-908334-28-1) in DMF (15 ml) was added NCS (1.07 g) and the mixture was stirred at 70° C. for 1 hour. The reaction mixture was then cooled to room temperature and poured into EtOAc and extracted sequentially with water and with saturated brine. The organic layer was dried over Na2SO4 and then concentrated in vacuo. The residue was purified by column chromatography (SiO2, gradient: 0% to 55% EtOAc in hexanes) to afford tert-butyl (RS)-3-(4-amino-3-chlorophenyl)pyrrolidine-1-carboxylate (1.16 g, 51%) as a yellow oil which was used in the next step without further purification. MS (ISP): 299.0 ([{37Cl}M+H]+), 297.2 ([{35Cl}M+H]+), 243.0 ([{37Cl}M+H—C4H8]+), 241.1 ([{35Cl}M+H—C4H8]+).

後処理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionextracted sequentially with water and with saturated brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (SiO2, gradient: 0% to 55% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-280683f9e61f4b5cabad774882068a1d
出典データセット
uspto-grants-2015_05
特許番号
US09029370B2

反応ノート

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