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Triethylsilane → cis-3-Benzyl-6-bromo-8-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene

HRID 1714142
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HRID 1714142 반응식
[CH2:1]([N:8]1[CH2:20][C@H:19]2[C@H:11]([C:12](=O)[C:13]3[C:18]2=[CH:17][C:16]([Br:21])=[CH:15][C:14]=3[CH3:22])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SiH](CC)(CC)CC>FC(F)(F)C(O)=O>[CH2:1]([N:8]1[CH2:20][C@H:19]2[C@H:11]([CH2:12][C:13]3[C:18]2=[CH:17][C:16]([Br:21])=[CH:15][C:14]=3[CH3:22])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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4

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HCID 12052TriethylsilaneHCID 16117545cis-3-Benzyl-6-bromo-8-methyl-1,2,3,4,4a,9a-hexahydro-3-aza-fluoren-9-one

생성물 1

HCID 16117547cis-3-Benzyl-6-bromo-8-methyl-2,3,4,4a,9,9a-hexahydro-1H-3-aza-fluorene수율 30.8%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

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온도
20 °C

실험 절차

To a solution of cis-3-Benzyl-6-bromo-8-methyl-1,2,3,4,4a,9a-hexahydro-3-aza-fluoren-9-one (1.5 g, 4.0 mmol) in trifluoroacetic acid (15 mL) was added Et3SiH (10 mL). The reaction mixture was stirred at 20° C. for 3 days then concentrated in vacuo. The residue was basified with NH4OH then extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed in silica gel column (Hex/EtOAc 9/1) to give the title compound (440 mg, 1.23 mmol): MS (ES) 356.1 (M+H).

후처리

  1. concentrationthen concentrated in vacuo
  2. extractionthen extracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed in silica gel column (Hex/EtOAc 9/1)

출처 및 근거

ORD 기록
ord-4b70eaf9b33948d79c89b24e25d309a1
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07795436B2

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