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Boron tribromide → N-Ethylcarbamate 5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 508499
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HRID 508499 반응식
B(Br)(Br)Br.[CH2:5]([NH:7][C:8](=[O:10])[O-:9])[CH3:6].C[O:12][C:13]1[C:14]([Cl:26])=[CH:15][C:16]2[CH:17]([CH3:25])[CH:18]3[CH2:22][NH:21][CH2:20][CH:19]3[C:23]=2[CH:24]=1>C(Cl)Cl>[CH2:5]([NH:7][C:8](=[O:9])[O-:10])[CH3:6].[OH:12][C:13]1[C:14]([Cl:26])=[CH:15][C:16]2[CH:17]([CH3:25])[CH:18]3[CH2:22][NH:21][CH2:20][CH:19]3[C:23]=2[CH:24]=1
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HCID 25134Boron tribromideHCID 86602844N-Ethylcarbamate 5-methoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

생성물 1

HCID 86602845N-Ethylcarbamate 5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

BBr3 (3.7 mL, 1.0 M in CH2Cl2) was added to a solution of N-ethylcarbamate-5-methoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 3, Step A) (0.49 g, 1.6 mmol) in CH2Cl2 (32 mL), and stirred overnight at room temperature. The excess BBr3 was quenched with the dropwise addition of H2O (10 mL), and washed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL). The organic extract was dried over MgSO4 and concentrated to afford the subtitle compound, which was used without further purification. MS calculated for C15H18ClNO3+H: 296, observed: 296.

후처리

  1. customThe excess BBr3 was quenched with the dropwise addition of H2O (10 mL)
  2. washwashed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-749ba946745a4fb09952126a742ec0ac
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096520B2

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