Sodium Hydroxide → 17-(3-Pyridyl)estra-1,3,5[10],16-tetraen-3-ol

HRID 1451366Notes

Reaction equation

C([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=O)C.[OH-].[Na+]>CO>[N:25]1[CH:26]=[CH:27][CH:28]=[C:23]([C:14]2[C@:15]3([CH2:17][CH2:18][C@H:19]4[C@@H:10]([CH2:9][CH2:8][C:7]5[CH:6]=[C:5]([OH:4])[CH:22]=[CH:21][C:20]=54)[C@@H:11]3[CH2:12][CH:13]=2)[CH3:16])[CH:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The method followed that described in Example 2, but using 3-acetoxy-17-(3-pyridyl)estra-1,3,5[10],16-tetraene (2.36 g, 6.3 mmol), methanol (40 ml), aqueous sodium hydroxide (10% w/v, 5 ml), and the mixture was heated at 80° C. for 10 min. Chromatography, on elution with toluene-methanol (8:1), afforded the title compound (1.40 g, 67%) which crystallised from toluene, m.p. 256°-258° C.: 1H-NMR(DMSO) inter alia δ1.01(3H,s,18-CH3), 6.15(1H,m,16-H), 6.47(1H,m,ArH), 6.52(1H,m,ArH), 7.04(1H,m,ArH), 7.35(1H,m,Py 5-H), 7.79(1H,m,Py 4-H), 8.45(1H,m,Py 6-H), 8.62(1H,m,Py 2-H). Anal. Calcd: C, 83.34; H, 7.60; N, 4.23. Found: C, 83.39; H, 7.78; N, 4.06%.

Workup

washChromatography, on elution with toluene-methanol (8:1)

Sources & evidence

ORD record: ord-ef63ae59d81f42629dad6612a152c876
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05604213

Reaction notes

Loading…