Water → HCID 86594671, compound

HRID 353707Notes

Reaction equation

[CH:1]([C@@H:3]1[CH2:20][C:19]2[C@H:14]([CH2:15][CH2:16][C:17](=O)[CH:18]=2)[C@@H:13]2[C@@H:4]1[C@H:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C@@H:8]([OH:22])[CH2:7][CH2:6]1)=[CH2:2].Cl.[NH2:24][OH:25].O>N1C=CC=CC=1>[CH:1]([C@@H:3]1[CH2:20][C:19]2[C@H:14]([CH2:15][CH2:16]/[C:17](=[N:24]\[OH:25])/[CH:18]=2)[C@@H:13]2[C@@H:4]1[C@H:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C@@H:8]([OH:22])[CH2:7][CH2:6]1)=[CH2:2].[CH:1]([C@@H:3]1[CH2:20][C:19]2[C@H:14]([CH2:15][CH2:16]/[C:17](=[N:24]/[OH:25])/[CH:18]=2)[C@@H:13]2[C@@H:4]1[C@H:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C@@H:8]([OH:22])[CH2:7][CH2:6]1)=[CH2:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (7α,17β)-7-ethenyl-17-hydroxyestr-4-en-3-one (Example 4; 1.63 g) in pyridine (9.4 ml) was added hydroxylamine hydrochloride (4.15 g). The reaction mixture was stirred at 80° C. for 50 min. After cooling, the mixture was poured into water (118 ml). The product was extracted into ethyl acetate; the combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography afforded (3E,7α,17β)-7-ethenyl-3-(hydroxyimino)estr-4-en-17-ol (0.60 g), [α]D20=−4.8° (c=1.00, dioxane), and (3Z,7α,17β)-7-ethenyl-3-(hydroxyimino)estr-4-en-17-ol (0.65 g), m.p. 206-224° C.

Workup

temperatureAfter cooling
extractionThe product was extracted into ethyl acetate
washthe combined organic phases were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-169e89d62e5d4598924aa6003f11f1b8
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06756366B1

Reaction notes

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