2,6-Lutidine → 3-Benzyloxy-10-[(tert-butyldimethylsilyl)oxy)-7,8,9,10-tetrahydro-phenanthridine

HRID 260389노트

반응식

HRID 260389 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:21]([CH:22]=1)=[N:20][CH:19]=[C:18]1[C:13]=2[CH:14]([OH:23])[CH2:15][CH2:16][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])(=O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:21]([CH:22]=1)=[N:20][CH:19]=[C:18]1[C:13]=2[CH:14]([O:23][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:15][CH2:16][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 150383433-Benzyloxy-10-hydroxy-7,8,9,10-tetrahydrophenanthridine

생성물 1

HCID 110802833-Benzyloxy-10-[(tert-butyldimethylsilyl)oxy)-7,8,9,10-tetrahydro-phenanthridine수율 98%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
25 °C

실험 절차

To a suspension of Compound 224 (1.10 g, 3.60 mmol) in dry CH2Cl2 (10 mL) under ice-cooling was added successively 2,6-lutidine (0.59 mL, 5.07 mmol) and tert-butyldimethylsilyl trifluromethanesulfonate (0.99 mL, 4.31 mmol), the resultant homogeneous solution was then stirred at 25° C. for 30 minutes. The reaction mixture was diluted with CH2Cl2 (20 mL), washed with brine, dried over anhydrous Na2SO4, and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel, ethyl ether-petroleum ether-benzene=1:2:2) to give Compound 225 (1.475 g, 98 percent): white solid; mp 123°-125° C.; Rf =0.50 (silica, 33 percent ethyl ether in benzene); IR (CHCl3) νmax 2952, 2933, 1621, 1506, 1336, 1295, 1256, 1240, 1174, 1151, 1090, 1025, 838 cm-1 ; 1H NMR (300 MHz, CDCl3) δ 8.61 (s, 1 H, H6), 7.98 (d, J=9.2 Hz, 1 H, H1), 7.55-7.48 (m, 3 H, H4 and aromatic), 7.46-7.34 (m, 3 H, aromatic), 7.27 (dd, J=9.2, 2.7 Hz, 1 H, H2), 5.42 (t, J=2.6 Hz, 1 H, H10), 5.20 (s, 2 H, benzylic), 3.04-2.93 (m, 1 H, H7), 2.87-2.72 (m, 1 H, H7), 2.26-2.05 (m, 2 H, H8 or H9), 1.92-1.76 (m, 2 H, H8 or H9), 0.84 (s, 9 H, SiC(CH3)3), 0.22 (s, 6 H, Si(CH3)2); MS (FAB+) m/e (rel intensity) 420 (M+H, 100), 362 (23), 330 (3), 288 (9); HRMS for C26H34NO2Si (M+H), calcd 420.2359, found 420.2360.

후처리

  1. temperaturecooling
  2. washwashed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography (silica gel, ethyl ether-petroleum ether-benzene=1:2:2)

출처 및 근거

ORD 기록
ord-fe8e20a06ef44650947040eb7bc7ee40
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05527805

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