Potassium Carbonate → 3-Benzyloxy-10-hydroxy-7,8,9,10-tetrahydrophenanthridine

HRID 260388Notes

Reaction equation

C([O:4][CH:5]1[C:18]2[C:9](=[CH:10][N:11]=[C:12]3[C:17]=2[CH:16]=[CH:15][C:14]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:13]3)[CH2:8][CH2:7][CH2:6]1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[CH2:20]([O:19][C:14]1[CH:15]=[CH:16][C:17]2[C:12]([CH:13]=1)=[N:11][CH:10]=[C:9]1[C:18]=2[CH:5]([OH:4])[CH2:6][CH2:7][CH2:8]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of Compound 223 (1.425 g, 4.10 mmol) in MeOH (25 mL) was added solid K2CO3 (120 mg, 0.87 mmol) followed by stirring at 25° C. for three hours. The solvent was removed in vacuo, the residue was purified by passing through a short column (silica gel, elution with ethyl ether) to furnish Compound 224 (1.23 g, 98 percent): white crystalline solid; mp 155°-157° C. (from CH2Cl2 -Et2O); Rf =0.12 (silica, 33 percent ethyl ether in benzene); IR (CHCl3) νmax 3602, 2948, 1620, 1507, 1455, 1348, 1298, 1242, 1150 cm-1 ; 1H NMR (300 MHz, CDCl3) δ 8.41 (s, 1 H, H6), 8.09 (d, J=9.2 Hz, 1 H, H1), 7.47 (d, J=6.9 Hz, 2 H, aromatic), 7.42-7.30 (m, 4 H, H4 and aromatic), 7.25 (dd, J=9.2, 2.9 Hz, 1 H, H2), 5.32 (t, J=3.5 Hz, 1 H, H10), 5.13 (s, 2 H, benzylic), 2.89-2.65 (m, 2 H, H7), 2.28-2.16 (m, 1 H, H8 or H9), 2.12-1.82 (m, 3 H, H8 and H9);MS (FAB+) m/e (rel intensity) 306 (M+H, 100), 290 (6); HRMS for C20H20NO2 (M+H), calcd 306.1494, found 306.1495. Anal. Calcd for C20H19NO2 : C, 78.66; H, 6.27; N, 4.59. Found: C, 78.80; H, 6.27; N, 4.50.

Workup

customThe solvent was removed in vacuo
customthe residue was purified
washby passing through a short column (silica gel, elution with ethyl ether)

Sources & evidence

ORD record: ord-4991cc58136e4e369e9f94c51e6bbe86
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05527805

Reaction notes

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