N-bromobutanimide → N-Ethylcarbamate 5-methyl-6-bromo-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 1517699ノート

反応式

HRID 1517699 の反応式
C1C(=O)N([Br:8])C(=O)C1.[CH2:9]([NH:11][C:12](=[O:14])[O-:13])[CH3:10].[CH3:15][C:16]1[CH:17]=[CH:18][C:19]2[CH:20]([CH3:28])[CH:21]3[CH2:25][NH:24][CH2:23][CH:22]3[C:26]=2[CH:27]=1>C(#N)C.C(Cl)Cl.O>[CH2:9]([NH:11][C:12](=[O:13])[O-:14])[CH3:10].[CH3:15][C:16]1[C:17]([Br:8])=[CH:18][C:19]2[CH:20]([CH3:28])[CH:21]3[CH2:25][NH:24][CH2:23][CH:22]3[C:26]=2[CH:27]=1

参加物

6

反応物 2

HCID 67184N-bromobutanimideHCID 86602856HCID 86602856、化合物

生成物 1

HCID 86602858N-Ethylcarbamate 5-methyl-6-bromo-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

NBS (34 mg, 0.2 mmol) was added to a solution of N-Ethylcarbamate-5-methyl-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 21, Step A) (50 mg, 0.2 mmol) in acetonitrile (1 mL), and stirred overnight at room temperature. The reaction was diluted with CH2Cl2 (3 mL) and H2O (3 mL) and filtered through an Extrelut column. The column was washed with CH2Cl2 and the filtrate was concentrated. The crude product was purified by column chromatography (SiO2) using a 0-50% EtOAc—hexanes gradient to afford the subtitle compound. MS calculated for C16H20BrNO2+H: 338, observed: 338.

後処理

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with CH2Cl2
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by column chromatography (SiO2)

出典と根拠

ORDレコード
ord-7d402f8be4414f358cbd5917909725e6
出典データセット
uspto-grants-2012_07
特許番号
US08232311B2

反応ノート

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