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

HRID 1197706Notes

Reaction equation

HRID 1197706 reaction equation
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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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 atmosphere (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 evaporated 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 dichloromethane); 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) δ9.99 (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), 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.

Workup

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

Sources & evidence

ORD record
ord-529587c73e894c7f9d761ec330c861f9
Source dataset
uspto-grants-1994_01
Patent number
US05276159

Reaction notes

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