Methanol → HCID 86735584, compound

HRID 1679768Notes

Reaction equation

HRID 1679768 reaction equation
[C:1]([O:4][C@@:5]1([C:25]#[CH:26])[CH:11]=[CH:10][C@H:9]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH2:7][CH3:8])[C@@H:20]1[C:15](=[CH:16][C:17](=O)[CH2:18][CH2:19]1)[CH2:14][CH2:13]3)(=[O:3])[CH3:2].CO.Cl.[NH2:30][OH:31].C(=O)(O)[O-].[Na+]>O>[C:1]([O:4][C@@:5]1([C:25]#[CH:26])[CH:11]=[CH:10][C@H:9]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH2:7][CH3:8])[C@@H:20]1[C:15](=[CH:16][C:17](=[N:30][OH:31])[CH2:18][CH2:19]1)[CH2:14][CH2:13]3)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 86735582Gestodene acetate

Product 1

HCID 86735584HCID 86735584, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

As described in Example 22, 2.4 g. of 17β-acetoxy-17α-ethynyl-18-methyl-4,15-estradien-3-one in 60 ml. of methanol and 2 ml. of water is reacted with 1.0 g. of hydroxylamine hydrochloride and 1.0 g. of sodium bicarbonate. After 1.5 hours, the reaction mixture is worked up analogously to Example 22. After the crude product has been chromatographed on silica gel with acetone-hexane, 760 mg. of 17β-acetoxy-17α-ethynyl-18-methyl-4,15-estradien-3-one oxime is obtained.

Workup

  1. customAfter the crude product has been chromatographed on silica gel with acetone-hexane, 760 mg

Sources & evidence

ORD record
ord-7ef2add8118b40b3a34d8d092697e9eb
Source dataset
uspto-grants-1978_03
Patent number
US04081537

Reaction notes

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