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Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181827
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HRID 2181827 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:15]([CH:16]=1)=[C:14]1[C:9]([CH:10]=[CH:11][CH:12]=[CH:13]1)=[N:8][C:7]=2[CH3:17].[BH4-].[Na+].FC(F)(F)C(O)=O.C1C=CC2C3C=CC=CC=3NCC=2C=1.C(N(CC)CC)C.[CH3:48][O:49][C:50]1[CH:55]=[CH:54][C:53]([S:56](Cl)(=[O:58])=[O:57])=[CH:52][C:51]=1[CH3:60]>O1CCCC1.ClCCl>[CH:4]1[CH:3]=[CH:16][C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][CH2:7][C:6]=2[CH:5]=1.[CH3:1][O:2][C:3]1[CH:16]=[C:15]2[C:6]([CH:7]([CH3:17])[N:8]([S:56]([C:53]3[CH:54]=[CH:55][C:50]([O:49][CH3:48])=[C:51]([CH3:60])[CH:52]=3)(=[O:58])=[O:57])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=32)=[CH:5][CH:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 2199665,6-DihydrophenanthridineHCID 4311764Sodium borohydrideHCID 159153174-Methoxy-3-methylbenzene-1-sulfonyl chlorideHCID 224823459-Methoxy-6-methylphenanthridine

생성물 2

HCID 219966
5,6-Dihydrophenanthridine
HCID 224822639-Methoxy-5-[(4-methoxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

The intermediate dihydrophenanthridine was prepared from 9-methoxy-6-methylphenanthridine, (Example 36, Step b, 0.7 g, 3.1 mmol), by treatment with sodium borohydride (0.48 g, 12.6 mmol) and trifluoroacetic acid (0.5 mL, 6.3 mmol) in tetrahydrofuran (35 mL). In a separate, second step, the dihydrophenanthridine was treated with triethylamine (1.1 mL, 7.9 mmol) and 4-methoxy-3-methylbenzenesulfonyl chloride (0.87 g, 3.9 mmol, 2 equivalents) in dichloromethane (10 mL) according to the procedure and in the same manner as described in Example 32, Method A, Step d. The crude product was purified by flash column chromatography on silica gel, eluting with a mixture of ethyl acetate-hexane (1:9 to 3:7 gradient), to yield 9-methoxy-5-[(4-methoxy-3-methylphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine as a homogeneous, white solid (0.27 g, 33% from the dihydrophenanthridine);

후처리

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with a mixture of ethyl acetate-hexane (1:9 to 3:7 gradient)

출처 및 근거

ORD 기록
ord-86443e47a7fc4280924e8e962e3ff1b5
출처 데이터셋
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06894061B2

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