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

HRID 546304노트

반응식

HRID 546304 반응식
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

참가 물질

6

반응물 2

HCID 67184N-bromobutanimideHCID 86602856HCID 86602856, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-16b510aa0d424ffaaa223d6d33c29be9
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935830B2

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