4-Methoxybenzenesulfonyl chloride → (S)-8-Fluoro-5-(4-methoxy-benzenesulfonyl)-6-methyl-5,6-dihydrophenanthridine

HRID 2224627노트

반응식

HRID 2224627 반응식
[F:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([CH3:16])[N:6]=[C:7]3[C:12]=2[CH:11]=[CH:10][CH:9]=[CH:8]3)[CH:3]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.B.CSC.B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.[OH-].[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]([S:25]([C:22]1[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=1)(=[O:27])=[O:26])[C@H:5]2[CH3:16]

참가 물질

7

반응물 5

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 12423031(Dimethyl sulfide)trihydroboronHCID 224823738-Fluoro-6-methylphenanthridine

생성물 1

HCID 58597403(S)-8-Fluoro-5-(4-methoxy-benzenesulfonyl)-6-methyl-5,6-dihydrophenanthridine수율 54%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 8-fluoro-6-methylphenanthridine (0.5 g, 2.4 mmol) and 4-methoxybenzenesulfonyl chloride (0.514 g, 2.49 mmol) in dichloromethane (5 mL) was added to a solution of borane-methyl sulfide (0.142 mL, 1.42 mmol, 10 M solution in methyl sulfide) and (R)-2-methyl-CBS-oxazaborolidine (0.47 mL, 0.4734 mmol, 1.0 M solution in toluene) in dry dichloromethane (6 mL) over the course of three hours at room temperature. The reaction mixture was stirred for twelve hours and then a solution of aqueous sodium hydroxide (10 mL, 1 N) was added. The aqueous layer was extracted with dichloromethane (3×). The organic layers were combined, washed with a solution of saturated, aqueous sodium chloride, and dried over anhydrous sodium sulfate. The organic solvent was removed in vacuo to yield the crude product as an orange solid. The crude product was purified by chromatography on silica gel (1:10 ethyl acetate:hexane) to afford the title compound as a white solid (0.489 g, 1.28 mmol, 54% ).

후처리

  1. extractionThe aqueous layer was extracted with dichloromethane (3×)
  2. washwashed with a solution of saturated, aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe organic solvent was removed in vacuo
  5. customto yield the crude product as an orange solid
  6. customThe crude product was purified by chromatography on silica gel (1:10 ethyl acetate:hexane)

출처 및 근거

ORD 기록
ord-029fac92e1e044278c10f1d5b032ee8a
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07378427B2

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