Water → HCID 86759646, compound

HRID 1815790Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (7α,14β,17α)-17-(hydroxymethyl)-7-methylestr4-en-3-one (Example 4; 1.0 g) in pyridine (6 ml) was added hydroxylamine hydrochloride (2.65 g). The reaction mixture was stirred at 80° C. for 1.5 h. After cooling, the mixture was poured into water. 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,14β,17α)-3-(hydroxyimino)-7-methylestr-4-ene-17-methanol (0.54 g), [α]D20=+95.5 ° (c=1.41, dioxane), and (3Z,7α,14β,17α)-3-(hydroxyimino)-7-methylestr-4-ene-17-methanol(0.28 g), [α]D20=+87.4 (c=1.0, dioxane).

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-f4913fc9c07d4967b0b228bbfe948954
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881728B1

Reaction notes

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