3-Benzyloxy-10-[(tert-butyldimethylsilyl)oxy)-7,8,9,10-tetrahydro-phenanthridine → 10-[(tert-Butyldimethylsilyl)oxy]-3-hydroxy-7,8,9,10-tetrahydrophenanthridine

HRID 1198791ノート

反応式

HRID 1198791 の反応式
C([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:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:15][CH2:16][CH2:17]1)C1C=CC=CC=1>CCO.[Pd]>[Si:24]([O:23][CH:14]1[C:13]2[C:18](=[CH:19][N:20]=[C:21]3[C:12]=2[CH:11]=[CH:10][C:9]([OH:8])=[CH:22]3)[CH2:17][CH2:16][CH2:15]1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

参加物

4

反応物 1

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

生成物 1

HCID 13576196710-[(tert-Butyldimethylsilyl)oxy]-3-hydroxy-7,8,9,10-tetrahydrophenanthridine収率 89.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A solution of Compound 225 (2.00 g, 4.77 mmol) in EtOH (80 mL) was hydrogenated over 10 percent Pd/C (1.00 g) under hydrogen atomsphere (ambient pressure) for four hours. The catalyst was removed by filtration through Celite with elution by 50 percent Et3N in THF (1.5 L). The combined filtrate was evaported in vacuo to provide Compound 141a (1.40 g, 89 percent): white crystalline solid; mp 248°-250° C. (dec., from MeOH-Et3N); Rf =0.48 (silica, 3.2 percent methanol in dicloromethane); IR (KBr) νmax 3400, 2929, 2857, 1622, 1619, 1611, 1477, 1404, 1249, 1238, 1212, 1088, 1034, 838, 773 cm-1 ; 1H NMR (300 MHz, CDCl3) δ 9.99 (br s, 1 H, ArOH), 8.52 (s, 1 H, H6), 7.91 (d, J=9.0 Hz, 1 H, H1), 7.20 (d, J=2.4 Hz, 1 H, H4), 7.14 (dd, J=9.0, 2.4 Hz, 1 H, H2), 5.43 (s, 1 H, H10), 2.95-2.84 (m, 1 H, H7), 2.79-2.65 (m, 1 H, H7), 2.14-2.04 (m, 1 H, H8 or H9), 2.00-1.87 (m, 1 H, H8 or H9), 1.86-1.65 (m, 2 H, H8 or H9), 0.79 (s, 9 H, SiC(CH3)3), 0.00 (s, 3 H, SiCH3), -0.02 (s, 3 H, SiCH3); MS (FAB+) m/e (rel intensity) 330 (M+H, 100), 272 (14), 198 (9); HRMS for C19H28NO2Si (M+H), calcd 330.1889, found 330.1890. Anal. Calcd for C19H27NO2Si: C, 69.26; H, 8.26; N, 4.25. Found: C, 69.10; H, 8.17; N, 4.16.

後処理

  1. customfor four hours
  2. customThe catalyst was removed by filtration through Celite with elution by 50 percent Et3N in THF (1.5 L)

出典と根拠

ORDレコード
ord-43bed7e802f84a15a096ed9179dc7280
出典データセット
uspto-grants-1994_01
特許番号
US05281710

反応ノート

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