ChemicalBook CAS DataBase List Progesterone

Progesterone synthesis

10synthesis methods

Product Name:Progesterone
CAS Number:57-83-0
Molecular formula:C21H30O2
Molecular Weight:314.46

Progesterone, pregn-4-en-3,20-dione (28.3.1), is made by oxidizing pregnenolon with aluminum isopropylate in the presence of cyclohexanone as a proton acceptor (Oppenauer oxidation). Pregnenolon itself is made by subsequent oxidation and further cleavage of the side chain of stigmasterin, a sterin of plant origin that is isolated from soybeans.

60966-36-1 Synthesis

60966-36-1
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57-83-0
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Yield:57-83-0 99%

Reaction Conditions:

with 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;oxygen;acetylacetone copper;N,N-diethylaniline in 1-methyl-pyrrolidin-2-one;N,N-dimethyl-formamide at 0; for 2 h;Inert atmosphere;Solvent;Reagent/catalyst;Temperature;

Steps:

4 Preparation of progesterone (1):

In a dry filled with nitrogen equipped with a thermometer,(2) (16.53 g; Fw: 330.50; 50 mmol) was added in a 250 mL three-necked flask,N, N-dimethylformamide (150 mL)Anhydrous acetylacetone copper (2.62 g; Fw: 261.76; 10.0 mmol)NMP (1.00 g; Fw: 99.13; 10.0 mmol)TEMPO (1.56 g; Fw: 156.25; 10.0 mmol)N, N-diethylaniline (1.49 g; Fw: 149.23; 10.0 mmol). The system temperature was then lowered to 0 ° C and the dry oxygen was introduced. With the oxygen into the system gradually become brown, in the oxygen into the process of continuous exotherm, maintaining the system temperature at 0 . After about 2.0 hours of introduction, after the reaction was completed, 2M hydrochloric acid was slowly added dropwise to the reaction system,pH to neutral, the organic phase was separated and the aqueous phase was extracted with methylene chloride. The organic phases were then combined with pale yellow syrup and treated with anhydrous sulfuric acid Magnesium dry. The solvent was concentrated under reduced pressure and then recrystallized from acetone to give 17.20 g of a white solid, yield: 99.0%.

References:

CN107129516,2017,A Location in patent:Paragraph 0030; 0031; 0032; 0033; 0034; 0035; 0036-0044

24254-01-1 Synthesis