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Trifluoroacetic acid → 5,6-Dihydrophenanthridine

HRID 2181825
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HRID 2181825 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][CH:51]=1>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:52]=[CH:51][C:50]([O:49][CH3:48])=[CH:55][CH:54]=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 74014-Methoxybenzenesulfonyl chlorideHCID 8471TriethylamineHCID 2199665,6-DihydrophenanthridineHCID 4311764Sodium borohydrideHCID 224823459-Methoxy-6-methylphenanthridine

생성물 2

HCID 219966
5,6-Dihydrophenanthridine
HCID 224823209-Methoxy-5-[(4-methoxyphenyl)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 (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 (1.0 mL, 7.5 mmol) and 4-methoxybenzenesulfonyl chloride (0.77 g, 3.7 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 1:4 gradient), to yield 9-methoxy-5-[(4-methoxyphenyl)sulfonyl]-6-methyl-5,6-dihydrophenanthridine as a homogeneous, white solid (0.45 g, 61% from the dihydrophenanthridine), m.p. 129-130° C.;

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 1:4 gradient)

출처 및 근거

ORD 기록
ord-9b4d2e4d86154742b7ae7f9b4ba3686e
출처 데이터셋
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06894061B2

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