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

HRID 53184Notes

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 (2.368, 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 δ 1.01(3H,s, 18-CH3),

Workup

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

Sources & evidence

ORD record: ord-39fed3d88a864be8859f4332024d53ad
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05618807

Reaction notes

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