84371-65-3

Basic information

• Product Name: Mifepristone
• Synonyms: 11-(4-(dimethylamino)phenyl)-17-hydroxy-17-(1-propynyl)-estra-9-dien-3-one;11beta-[4-(n,n-dimethylamino)phenyl]-17alpha-(prop-1-ynyl)-delta4,9-estradiene;17-beta)-(11-bet;17beta)-11-[4-(dimethylamino)-phenyl]-17-hydroxy-17-(1-propynyl)estra-(11bet;17-beta-hydroxy-11-beta-(4-dimethylaminophenyl-1)-17-alpha-(prop-1-ynyl)oest;-17beta-ol-3-one;4,9-dien-3-one;r38486
• CAS NO: 84371-65-3
• Molecular Formula: C₂₉H₃₅NO₂
• Molecular Weight: 429.59
• EINECS: 1806241-263-5
• Product Categories: Steroids;Hormone;Acetylenes;Biochemistry;Functionalized Acetylenes;Hydroxyketosteroids;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Intracellular receptor;Nuclear Receptors;Steroid and Hormone;API;Hormone Drugs
• Mol File: 84371-65-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 195-198°C
• Boiling Point: 544.13°C (rough estimate)
• Flash Point: 334 °C
• Appearance: pale yellow solid
• Density: 1.0731 (rough estimate)
• Vapor Pressure: 1.14E-16mmHg at 25°C
• Refractive Index: 1.6290 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 20 mg/ml).
• PKA: 12.94±0.60(Predicted)
• Water Solubility: 474.8ug/L(22.5 oC)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
• Merck: 14,6186
• CAS DataBase Reference: Mifepristone(CAS DataBase Reference)
• NIST Chemistry Reference: Mifepristone(84371-65-3)
• EPA Substance Registry System: Mifepristone(84371-65-3)

Safety Data

• Hazard Codes: T
• Statements: 60-61
• Safety Statements: 53-22-36/37/39-45
• WGK Germany: 3
• RTECS: KG2955000
• Hazardous Substances Data: 84371-65-3(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 84371-65-3 differently. You can refer to the following data:
1. Mifepristone is a kind of antagonist of the progestational and glucocorticoid hormone. It is mainly used for the treatment of hypercortisolism in patients with nonpituitary cushing syndrome. During the treatment of Cushing’s syndrome, mifepristone takes effect through interfering with the binding of cortisol to its receptor. It reduces the effects of excess cortisol (e.g., high blood sugar levels) without causing decreased cortisol production. It can also be used to end a pregnancy. Its inhibition on progesterone can induce bleeding during the luteal phase and in early pregnancy.
2. Mifepristone is an orally-active progesterone and glucocorticoid receptor antagonist indicated for use as a post-coital contraceptive. In addition to being an abortifacient, mifepristone is reported to be effective in the treatment of ocular hypertension; its potential therapeutic effect in hormone-dependent tumors is currently under investigation.

Chemical Properties

Pale Yellow Solid

Originator

Roussel-Uclaf (France)

Uses

Different sources of media describe the Uses of 84371-65-3 differently. You can refer to the following data:
1. glutamate uptake inhibitor, AMPA blocker
2. A progesterone and glucocorticoid antagonist, suppresses VEGF production.
3. A progesterone receptor antagonist with partial agonist activity. Abortifacient.
4. Mifepristone is a progesterone receptor antagonist with partial agonist activity. Abortifacient.

Indications

Mifepristone is a progesterone receptor antagonist that has a high affinity for glucocorticoid receptors and little agonist effect.This drug has recently been approved for use in the United States for the treatment of hypercortisolism. At high doses, mifepristone blocks negative feedback of the hypothalamic–pituitary axis, thereby increasing endogenous corticotrophin and cortisol levels. Because mifepristone exerts its effects at the receptor level and not by altering glucocorticoid production, elevated serum cortisol and corticotrophin levels may not accurately reflect the effectiveness of the therapeutic regimen. Mifepristone does not inhibit cortisol binding to the mineralocorticoid receptor, so that the resulting corticotrophin disinhibition may cause potassium depletion. Thus, administration of a mineralocorticoid receptor antagonist such as spironolactone may be indicated with mifepristone. Hypoadrenalism, nausea, and drowsiness have been reported during prolonged administration of mifepristone.

Manufacturing Process

1st method of synthesis of mifepristone:A solution of 24 g of 4-(N,N-dimethylaminoethoxy)bromobenzene was addeddropwise over 45 min to magnesium in 90 ml of anhydrous tetrahydrofuran. 2ml of 1,2-dibromoethane were added as catalyst. After the addition, themixture was stirred at 25°C for one hour to obtain a solution of 0.7 M of 4-(N,N-dimethylaminoethoxy)-benzene magnesium bromide which was thenadded to a solution of 6.16 g of dimethylsulfide-cuprous bromide complex in20 ml of tetrahydrofuran. The mixture was stirred at room temperature for 20min and a solution of 3.7 g of 3,3-[1,2-(ethanediyl-bisoxy)]-5α,10α-epoxy-17α-prop-1-ynyl-δ(9(11))-estrene-17β-ol in 50 ml of tetrahydrofuran was addedthereto dropwise over a few minutes. The mixture was stirred under an inertatmosphere for one hour and was then poured into a solution of 15 g ofammonium chloride in 20 ml of iced water. The mixture was extracted withether and the organic phase was washed with aqueous saturated sodiumchloride solution, was dried and evaporated to dryness under reducedpressure. The 18.3 g of oil were chromatographed over silica gel and elutedwith chloroform to obtain 4.5 g of 3,3-[1,2-ethanediyl-bisoxy]-11β-[4-(N,N-dimethylaminoethoxy)phenyl]-17α-(prop-1-ynyl)-δ9-estrene-5α,17β-diol with aspecific rotation of [α]D20=-44(+/-)1.5° (c = 1% in chloroform).9.5 ml of 2 N hydrochloric acid were added to a solution of 4.5 g of 3,3-[1,2-ethanediyl-bisoxy]-11β-[4-(N,N-dimethylaminoethoxy)phenyl]-17α-(prop-1-ynyl)-δ9-estrene-5α,17β-diol in 20 ml of methanol and the solution was stirredat room temperature for 2 hours. 260 ml of ether and 110 ml of an aqueoussaturated sodium bicarbonate solution were added to the mixture which wasstirred at room temperature for 15 min. The decanted aqueous phase wasextracted with ether and the organic phase was dried and evaporated todryness under reduced pressure. The 3.3 g of residue were chromatographedover silica gel and eluted with a 92.5/7.5 methylene chloride-methanolmixture to obtain 1.8 g of amorphous 11β-[4-(N,N-dimethylaminoethoxy)phenyl]-17α-(prop-1-ynyl)-δ4,9-estradiene-17β-ol-3-one with a specificrotation of [α]D20=+71° (c = 1% in chloroform).2th method of synthesis of mifepristone (see scheme):The oxidation of the diene I, which constitutes an intermediate for totalsynthesis of 19-nor steroids, with a reagent prepared from trifluoroaceticanhydride/hydrogen peroxide was obtained exclusively α-epoxide II. Thecondensation of II with the Grignard reagent from 4-bromo-N,N-dimethylaniline results in addition of the reagent at the 11β-position. Thisresults in rearragement of the olefin to 9,10 and opening of the epoxide. Thestereochemistry of the product obtained III is consistent with trans-opening ofthe oxirane, albeit at a remove of two carbon atoms. Mild hydrolysis removesthe silyl cyanohydrin protecting group at the 17-position to give a ketone IV.Reaction of the ketone with propargyl lithium leads to V. Hydrolysis of thatproduct under more strenuous condition results in removal of the acetal at 3;the resulting β-hydroxyketone then dehydrates to afford the 4,10(9)-dienoneVI. Another name of VI is estra-4,9-dien-3-one, 11-(4-(dimethylamino)phenyl)-17-hydroxy-17-(1-propynyl)-, (11β,17β)- or mifepristone.

Brand name

Mifeprex (Danco);Ru-486;Mifegyne.

Therapeutic Function

Antiprogesterone

World Health Organization (WHO)

Mifepristone, an antiprogesterone used in combination with a prostaglandin for the termination of early pregnancy, was introduced in 1990. Use of the combination has been associated with episodes of coronary spasm that are attributed to administration of the prostaglandin and which have resulted in several cases of cardiac infarction and ventricular fibrillation. At least one of these incidents has been fatal.

Biological Activity

Selective antagonist at progesterone (PR) and glucocorticoid (GR) receptors in vitro and in vivo . Is a silent antagonist at PR and has a higher affinity than progesterone. Has higher affinity for GR than dexamethasone.

Biochem/physiol Actions

Therefore, mifepristone is considered to be a potent abortifacient. It is also known to inhibit human chorionic gonadotropin. Mifepristone results in decidual necrosis.

Pharmacokinetics

Following oral administration, mifepristone is rapidly absorbed, with a peak plasmaconcentration in approximately 90 minutes , an oral bioavailability of approximately 70%, and a term inal elimination half-life of 18 hours. It is 98% protein bound, primarily to album in and α1-acid glycoprotein. Mifepristone is metabolized primarily via CYP3A4 pathways involving mono- and di-N-demethylation and terminal hydroxylation of the 17-propynyl chain. The fact that approximately 83% of the drug is recovered in the feces and 9% in the urine suggests a biliary route of elimination. Mifepristone also demonstrates antiglucocorticoid activity.

Clinical Use

An antiprogestin is a substance that competes with progesterone for its receptor and, ultimately, prevents progesterone from binding to and activating its receptor. Because progesterone is integral to the continuation of an early pregnancy, it is expected that antipro-gestins will interfere with pregnancy maintenance. In 1982, the first antiproges tin, mifepristone (RU 486), was reported. Mifepristone was shown to interrupt early stages of implantation and pregnancy in humans.

References

https://pubchem.ncbi.nlm.nih.gov/compound/mifepristone#section=Top https://www.drugbank.ca/drugs/DB00834 https://www.drugs.com/cdi/mifepristone-tablets.html

InChI:InChI=1/C29H35NO2/c1-5-15-29(32)16-14-26-24-12-8-20-17-22(31)11-13-23(20)27(24)25(18-28(26,29)2)19-6-9-21(10-7-19)30(3)4/h6-7,9-10,17,24-26,32H,8,11-14,16,18H2,1-4H3/t24?,25-,26?,28+,29+/m1/s1

Synthetic route

mifepristone (84371-65-3) → aglepristone

Conditions	Yield
With hydrogen In methanol under 3800.26 Torr; Reagent/catalyst; Solvent; Green chemistry; stereoselective reaction;	99%

2-Picolinic acid (98-98-6) + mifepristone (84371-65-3) → N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylpicolinamide

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	98%

tri-n-butyl-tin hydride (688-73-3) + mifepristone (84371-65-3) → C41H63NO2Sn

Conditions	Yield
With [MoI2(CO)2(CNC6H3(C6H3iPr2-2,6)2-2,6)2] In benzene-d6 at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Glovebox;	98%

mifepristone (84371-65-3) → Demethylmifepristone (104004-96-8)

Conditions	Yield
With lithium acetate; iodine In tetrahydrofuran; methanol at 0 - 20℃; for 24h; Reagent/catalyst; Temperature; Solvent;	97%
With lithium acetate; iodine In tetrahydrofuran; methanol at 20℃;	92%
With iodine; calcium oxide In tetrahydrofuran; methanol at 0℃; for 1h;	82%

mifepristone (84371-65-3) + chloroacetyl chloride (79-04-9) → 2-chloro-N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylacetamide

Conditions	Yield
With triethylamine In ethyl acetate at 0 - 20℃; for 16h;	92%

trifluoromethylsulfonic anhydride (358-23-6) + methyl (3β,5β,7α,12α)-7,12-dixydroxy-3-(2-hydroxyethoxy)cholan-24-oate (135053-66-6) + mifepristone (84371-65-3) → methyl (3β,5β,7α,12α)-7,12-dihydroxy-3-{2-[{4-[(11β,17α)-17-hydroxy-3-oxo-17-prop-1-ynylestra-4,9-dien-11-yl]phenyl}(methyl)amino]ethoxy}cholan-24-oate (639520-78-8)

Conditions	Yield
Stage #1: trifluoromethylsulfonic anhydride; methyl (3β,5β,7α,12α)-7,12-dixydroxy-3-(2-hydroxyethoxy)cholan-24-oate With N-ethyl-N,N-diisopropylamine In dichloromethane at -55 - -45℃; for 3.28333h; Stage #2: mifepristone In dichloromethane at -6℃; for 88h; Stage #3: With N-ethyl-N,N-diisopropylamine; sodium iodide In acetonitrile for 45h; Heating / reflux;	82.7%

mifepristone (84371-65-3) + benzoic acid (65-85-0) → N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylbenzamide

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	77%

4'-Hydroxybiphenyl-4-carboxylic acid (58574-03-1) + mifepristone (84371-65-3) → N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methyl-[1,1'-biphenyl]-4-carboxamide

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	73%

3,4-dichlorbenzoic acid (51-44-5) + mifepristone (84371-65-3) → 3,4-dichloro-N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylbenzamide

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	71%

triphenylboroxine (3262-89-3) + mifepristone (84371-65-3) → (8S,11R,13S,14S)-11-(4-(dimethylamino)phenyl)-13-methyl-17-((S)-2-phenylprop-1-en-1-ylidene)-6,7,8,11,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

Conditions	Yield
With [Rh(OH)(cod)]2 In tetrahydrofuran at 75℃; for 12h; Inert atmosphere; diastereoselective reaction;	69%

4-trifluoromethylphenylboronic acid (128796-39-4) + mifepristone (84371-65-3) → (8S,11R,13S,14S,17R)-11-(4-(dimethylamino)phenyl)-17-hydroxy-13-methyl-17-((E)-2-(4-(trifluoromethyl)phenyl)prop-1-en-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one

Conditions	Yield
With water; 8CO*2Br(1-)*2Mn(1+); potassium hydrogencarbonate In toluene; pentane at 90℃; for 0.25h; Sealed tube; regioselective reaction;	68%

2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) + mifepristone (84371-65-3) → (8S,11R,13S,14S,17S)-11-(4-((2-chlorophenyl)(methyl)amino)phenyl)-17-hydroxy-13-methyl-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one

Conditions	Yield
With tetrachloromethane; potassium fluoride; 18-crown-6 ether In tetrahydrofuran at 65℃; for 10h; Sealed tube;	67%

mifepristone (84371-65-3) → Demethylmifepristone (104004-96-8) + N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylformamide (639520-83-5)

Conditions	Yield
Stage #1: mifepristone With 1,4-diaza-bicyclo[2.2.2]octane; rose bengal; acetic acid In acetonitrile at 20℃; for 1.5h; Flow reactor; Irradiation; Stage #2: With ascorbic acid In water; acetonitrile at 20℃; for 2h;	A 65% B 22%

mifepristone (84371-65-3) → N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylformamide (639520-83-5)

Conditions	Yield
With N-methyl-2-indolinone; tetrapropylammonium perruthennate In dichloromethane at 0℃; for 0.333333h;	63%
Stage #1: mifepristone With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide In dichloromethane at -10℃; Stage #2: With sodium disulfite In dichloromethane; water at -10 - 20℃; for 0.5h;	63%

N-phenyl-maleimide (941-69-5) + mifepristone (84371-65-3) → (3aR*,9bS*)-8-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)-5-methyl-2-phenyl-3a,4,5,9b-tetrahydro-1H-pyrrolo[3,4-c]quinoline-1,3(2H)-dione

Conditions	Yield
With chloropyridinecobaloxime(III); Ru(bpy)3Cl2*6H2O In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation;	62%

mifepristone (84371-65-3) + 4-chloro-2-fluorobenzoic acid (446-30-0) → 5-chloro-2-fluoro-N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylbenzamide

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 30h;	61%

methyl (3β,5β,7α,12α)-7,12-dihydroxy-3-[2-(iodo)ethoxy]cholan-24-oate (639520-81-3) + mifepristone (84371-65-3) → methyl (3β,5β,7α,12α)-7,12-dihydroxy-3-{2-[{4-[(11β,17α)-17-hydroxy-3-oxo-17-prop-1-ynylestra-4,9-dien-11-yl]phenyl}(methyl)amino]ethoxy}cholan-24-oate (639520-78-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 80℃; for 19h;	60.6%

diazoacetic acid ethyl ester (623-73-4) + mifepristone (84371-65-3) → C33H40N4O4

Conditions	Yield
With 1-hydroxy-1,2-benzodioxol-3-(1H)-one; trimethylsilylazide In acetonitrile at 20℃; Inert atmosphere; chemoselective reaction;	54%

mifepristone (84371-65-3) → C29H33NO2 (1356033-06-1)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetic acid at 20℃; for 1h; Sonication;	41%

mifepristone (84371-65-3) → C29H32Cl3NO2 (1356033-08-3)

Conditions	Yield
With 1,3,5-trichloro-2,4,6-triazine In acetonitrile at 20℃; for 48h;	41%

3-iodo-N-((5-methylfuran-2-yl)methyl)propanamide + mifepristone (84371-65-3) → C37H44N2O4

Conditions	Yield
In acetonitrile at 120℃; for 2h; Microwave irradiation;	40%

ethyl 4-iodobutyrate (7425-53-8) + mifepristone (84371-65-3) → C34H43NO4

Conditions	Yield
In acetonitrile at 120℃; for 1h; Microwave irradiation;	36%

mifepristone (84371-65-3) → 6α-hydroxy-mifepristone + 6β-hydroxy-mifepristone

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane at 80℃; for 20h;	A 4% B 35%

mifepristone (84371-65-3) → C28H33NO5 (1356033-03-8)

Conditions	Yield
With dihydrogen peroxide In dichloroethane at 20℃; for 4h;	32%

mifepristone (84371-65-3) → C28H31NO3 (1356033-05-0)

Conditions	Yield
With Cumene hydroperoxide; C44H24FeN8O8 In dichloroethane at 20℃; for 6h;	19%

mifepristone (84371-65-3) → (8S,11R,13S,14S,17S)-11-(3,5-dichloro-4-(dimethylamino)phenyl)-17-hydroxy-13-methyl-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one

Conditions	Yield
With trichloroisocyanuric acid In dichloromethane at 20℃; for 15h;	18%

mifepristone (84371-65-3) → <5R,7Ξ,8R,8aR>-5-<4-(dimethylamino)phenyl>-4,5,6,7,8,8a,9,10-octahydro-7-methyl-8-(3-oxo-4-hexinyl)-2(3H)-phenanthrenone + Demethylmifepristone (104004-96-8)

Conditions	Yield
for 336h; Irradiation; photodecomposition in crystalline state; other times;	A 0.2% B 0.5%
for 336h; Irradiation;	A 0.2% B 0.5%

mifepristone (84371-65-3) + O-(6-aminohexyl)hydroxylamine → 11-(4-dimethylamino-phenyl)-17-hydroxy-13-methyl-17-prop-1-ynyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one syn-O-(6-aminohexyl)oxime + 11-(4-dimethylamino-phenyl)-17-hydroxy-13-methyl-17-prop-1-ynyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one anti-O-(6-aminohexyl)oxime

Conditions	Yield
In ethanol at 20℃; for 2h; Title compound not separated from byproducts;

mifepristone (84371-65-3) → N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylacetamide

Conditions	Yield
Multi-step reaction with 3 steps 1: 63 percent / NMO; tetra-n-propylammonium perruthenate / CH2Cl2 / 0.33 h / 0 °C 2: 86 percent / aq. HCl / methanol / 40 h / 20 °C 3: pyridine / 2 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: lithium acetate; iodine / tetrahydrofuran; methanol / 20 °C 2: triethylamine / ethyl acetate / 16 h / 0 - 20 °C / Inert atmosphere View Scheme

mifepristone (84371-65-3) → (S)-2-Amino-4-{[4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-prop-1-ynyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)-phenyl]-methyl-carbamoyl}-butyric acid methyl ester (734523-73-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 63 percent / NMO; tetra-n-propylammonium perruthenate / CH2Cl2 / 0.33 h / 0 °C 2: 86 percent / aq. HCl / methanol / 40 h / 20 °C 3: 0.93 g / TBTU; diisopropylethylamine / dimethylformamide / 48 h / 20 °C 4: HCl / ethyl acetate / 1 h View Scheme

Downstream Products

• 104004-96-8 (8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-11-(4-(methylamino)phenyl)-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one 

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