566-65-4

Basic information

• Product Name: 5-alpha-Dihydroprogesterone
• Synonyms: ALLOPREGNANE-3,20-DIONE;ALLOPREGNAN-3,20-DIONE;ALLOPREGNANDIONE;(5S,8R,9S,10S,13S,14S,17S)-17-ACETYL-10,13-DIMETHYL-HEXADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-3-ONE;5 A-PREGNANE-3 20-DIONE;5A-PREGNAN-3,20-DIONE;5ALPHA-PREGNANE-3,20-DIONE (ALLO);5ALPHA-DIHYDROPROGESTERONE
• CAS NO: 566-65-4
• Molecular Formula: C21H32O2
• Molecular Weight: 316.48
• EINECS: 209-297-3
• Product Categories: Steroids
• Mol File: 566-65-4.mol
• Article Data: 30

Chemical Properties

• Melting Point: 200 °C
• Boiling Point: 429.2 °C at 760 mmHg
• Flash Point: 160.3 °C
• Appearance: /
• Density: 1.048 g/cm³
• Vapor Pressure: 1.43E-07mmHg at 25°C
• Refractive Index: 1.515
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 5-alpha-Dihydroprogesterone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-alpha-Dihydroprogesterone(566-65-4)
• EPA Substance Registry System: 5-alpha-Dihydroprogesterone(566-65-4)

Safety Data

• WGK Germany: 3
• RTECS: TU4157150
• Hazardous Substances Data: 566-65-4(Hazardous Substances Data)

Usage

Description

5α-Dihydroprogesterone?(5α-DHP) is an?endogenous?progestogen?and?neurosteroid?that is?synthesized?from?progesterone.It is also an?intermediate?in the synthesis of?allopregnanolone?and?isopregnanolone?from progesterone.

In vitro

5a-Pregnane-3,20-dione decreases cell-substrate attachment, adhesion plaques, vinculin expression, and polymerizes F-actin in MCF-7 breast cancer cells.

Uses

(5α)-Pregnane-3,20-dione exerts neuroprotective effects in chronic autoimmune encephalomyelitis (EAE). The neuroactivity of the steroid acts as a therapeutic agent for multiple sclerosis.

Definition

ChEBI: 5alpha-pregnane-3,20-dione is a C21-steroid hormone that is 5alpha-pregnane substituted by oxo groups at positions 3 and 20. It is a metabolite of progestrone. It has a role as a human metabolite and a progestogen. It is a 20-oxo steroid, a C21-steroid hormone and a 3-oxo-5alpha-steroid. It is functionally related to a progesterone. It derives from a hydride of a 5alpha-pregnane.

Biochem/physiol Actions

(5α)-Pregnane-3,20-dione is a high-level metabolite of progesterone in breast cancer tissue (but not normal breast tissue); promotes cell proliferation and detachment. Receptors appear only on the cell surface of MCF-7 breast cancer cells, not on nuclei where most other steroid receptors are located.

InChI:InChI=1/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1

Synthetic route

(20R)-5α-Pregnandiol-(3β.20) (516-53-0) → dihydroprogesterone (566-65-4)

Conditions	Yield
With Jones reagent In acetone at 10℃;	96%
With chromium(VI) oxide; acetic acid

3β-methoxy-5α-pregnane-20-one (7680-01-5) → dihydroprogesterone (566-65-4)

Conditions	Yield
With 3,3-dimethyldioxirane In acetone for 18h; Ambient temperature;	95%

5α-pregnanedione-(3,20)-dioxime (6170-12-3) → dihydroprogesterone (566-65-4)

Conditions	Yield
With acetyl chloride; sodium nitrite In dichloromethane at 20℃;	90%

Progesterone (57-83-0) → dihydroprogesterone (566-65-4) + 20-hydroxy-Δ4-progest-3-one (15114-79-1)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; methylcopper; diisobutylaluminium hydride In tetrahydrofuran; diethyl ether; hexane at -50℃; for 2h;	A 84% B 5.9%

1-((3S,5S,8R,9S,10S,13S,14S,17S)-3-Benzyloxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanone → dihydroprogesterone (566-65-4)

Conditions	Yield
With 3,3-dimethyldioxirane In acetone for 18h; Ambient temperature;	82%

isopregnanolone (516-55-2) → dihydroprogesterone (566-65-4)

Conditions	Yield
With sodium hypochlorite; acetic acid; sodium bromide In tetrahydrofuran at 20 - 40℃; for 2h;	81%
With sodium hypochlorite; sodium bromide In water; acetic acid at 20℃; for 2h;	79%
With chromium(VI) oxide; acetic acid

Progesterone (57-83-0) → dihydroprogesterone (566-65-4) + pregnanedione (128-23-4) + allopregnanolone (40135-22-6) + 3-hydroxy-5β-pregnan-20-one (4320-08-5)

Conditions	Yield
With hydrogen; Cu/Al2O3 In toluene at 60℃; under 760 Torr;	A 14% B 49% C 2% D 8%

Progesterone (57-83-0) → dihydroprogesterone (566-65-4)

Conditions	Yield
In ethanol at 24 - 26℃; for 96h; Penicillium decumbens ATCC 10436, potato dextrose broth;	45%
With Chlorella vulgaris C211/8k; 4,4'-butylidenebis(6-tert-butyl-m-cresol) at 20℃; for 360h; Reduction; illumination;	17.3%
With Penicillium digitatum MRC 500787; MYB medium (malt extract 2percent, glucose 1percent, bacteriological peptone 1percent, yeast extract 0.3percent) In N,N-dimethyl-formamide at 24℃; for 120h;	12.3%

dihydrocholesterone (566-88-1) → dihydroprogesterone (566-65-4) + 5α-cholestane-3,11-dione (69483-56-3) + 5α-cholestane-3,6-dione (2243-09-6) + 3,7-dioxo-5α-cholestane (13400-67-4)

Conditions	Yield
With pyridine; oxygen; acetic acid; zinc; iron In water for 5h; Ambient temperature; Gif system; Further byproducts given;	A 4.6% B 1.1% C 4.1% D 3.8%

dihydrocholesterone (566-88-1) → dihydroprogesterone (566-65-4) + 5α-cholestane-3,6-dione (2243-09-6) + 3,7-dioxo-5α-cholestane (13400-67-4) + (5S,8R,9S,10S,13S,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-tetradecahydro-cyclopenta[a]phenanthrene-3,16-dione (108393-74-4)

Conditions	Yield
With pyridine; oxygen; acetic acid; zinc; iron In water for 5h; Ambient temperature; Gif system; Further byproducts given;	A 4.6% B 4.1% C 3.8% D 2.1%

dihydrocholesterone (566-88-1) → dihydroprogesterone (566-65-4) + 5α-cholestane-3,6-dione (2243-09-6) + 3,7-dioxo-5α-cholestane (13400-67-4) + (5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-tetradecahydro-cyclopenta[a]phenanthrene-3,12-dione (41882-89-7)

Conditions	Yield
With pyridine; oxygen; acetic acid; zinc; iron In water for 5h; Ambient temperature; Gif system; Further byproducts given;	A 4.6% B 4.1% C 3.8% D 1%

dihydrocholesterone (566-88-1) → dihydroprogesterone (566-65-4) + 5α-cholestane-3,6-dione (2243-09-6) + 3,7-dioxo-5α-cholestane (13400-67-4) + 5α,14α-cholestane-3,15-dione (73389-50-1)

Conditions	Yield
With pyridine; oxygen; acetic acid; zinc; iron In water for 5h; Ambient temperature; Gif system; Further byproducts given;	A 4.6% B 4.1% C 3.8% D 3.3%

methanol (67-56-1) + (5α,17βH)-pregnane-3,20-dione (51154-65-5) + sodium methylate (124-41-4) → dihydroprogesterone (566-65-4)

1-(3-Hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethanone (145-13-1, 566-63-2, 19037-28-6, 38372-24-6) → dihydroprogesterone (566-65-4)

Conditions	Yield
With palladium on activated charcoal Hydrogenation.anschliessende Oxidation mit CrO3;

Progesterone (57-83-0) → dihydroprogesterone (566-65-4) + pregnanedione (128-23-4)

Conditions	Yield
With hydrogen; palladium In pyridine at 25℃; under 760 Torr; Rate constant; selectivity to 5β compound;
With hydrogen bromide; hydrogen; palladium In tetrahydrofuran at 25℃; under 760 Torr; Rate constant; selectivity to 5β compound;
With acetic acid; platinum Hydrogenation.Behandlung des Reaktionsprodukts mit CrO3 in Essigsaeure bei 15-20grad;

Pregnenolone (145-13-1) → dihydroprogesterone (566-65-4)

Conditions	Yield
With acetic acid; platinum Hydrogenation.anschliessende Behandlung mit CrO3 in Essigsaeure;
Multi-step reaction with 2 steps 1: 90 percent / H2 / Pd/C / tetrahydrofuran; acetic acid / 8 h / 50 - 60 °C / 3102.89 Torr 2: 79 percent / NaOCl; NaBr / acetic acid; H2O / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 12 h / 40 °C / 2327.23 Torr 2: Dess-Martin periodane / dichloromethane / 3 h / 0 - 25 °C View Scheme
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen; acetic acid / tetrahydrofuran / 60 °C / 3102.97 Torr 2: acetic acid; sodium bromide; sodium hypochlorite / tetrahydrofuran / 2 h / 20 - 40 °C View Scheme

Pregnenolone acetate (1778-02-5) → dihydroprogesterone (566-65-4)

Conditions	Yield
With acetic acid; platinum Hydrogenation.Erhitzen des Hydrierungsprodukts mit methanol. KOH und Behandeln des Reaktionsprodukts mit CrO3 in Essigsaeure bei 20grad;
Multi-step reaction with 3 steps 1: H2 / 10 percent Pd/C View Scheme

isopregnanolone (516-55-2) → dihydroprogesterone (566-65-4) + 20-oxo-2,3-seco-5α-pregnanedioic acid-(2,3) (26654-59-1)

Conditions	Yield
With chromium(VI) oxide; acetic acid

5α-pregnan-3β,20α-diol (566-56-3) → dihydroprogesterone (566-65-4)

Conditions	Yield
With chromium(VI) oxide; acetic acid

5α-pregnane-3α,20α-diol (566-58-5) → dihydroprogesterone (566-65-4)

Conditions	Yield
With chromium(VI) oxide; acetic acid

tetrahydroprogesterone (516-54-1) → dihydroprogesterone (566-65-4)

Conditions	Yield
With chromium(VI) oxide; acetic acid
With NAD:3α-hydroxy-5α-pregnane-20-one oxidoreductase; NAD at 37℃;
With oxygen; sodium acetate In water; Diethyl carbonate at 100℃; under 37503.8 Torr; for 4h; Autoclave;

5α-H-pregn-16-ene-3,20-dione (13164-11-9) → dihydroprogesterone (566-65-4)

Conditions	Yield
With Pd-BaSO4; diethyl ether Hydrogenation;
With Pd-BaSO4; ethanol Hydrogenation;
With acetic acid; zinc at 100℃;

Progesterone (57-83-0) → dihydroprogesterone (566-65-4) + pregnanedione (128-23-4) + Androstenedione (63-05-8) + 17-hydroxyprogesterone (68-96-2)

Conditions	Yield
With D-glucose; Dulbecco phosphate buffer at 37℃; for 22h; Product distribution; metabolism after incubation of blastoderms of fertilized eggs of White Leghorn hens;

Progesterone (57-83-0) → dihydroprogesterone (566-65-4) + isopregnanolone (516-55-2) + (20S)-20-hydroxypregn-4-en-3-one (145-14-2) + 5α-pregnan-3β,20α-diol (566-56-3)

Conditions	Yield
With Tris buffer at 37℃; for 2h; Product distribution; metabolism in human endometrial adenocarcinoma cells (HEC-1 line), 14C- and 3H-labeled in dependence on time;

Pregnenolone (145-13-1) → Progesterone (57-83-0) + dihydroprogesterone (566-65-4) + pregnanedione (128-23-4)

Conditions	Yield
With D-glucose; Dulbecco phosphate buffer at 37℃; for 22h; Product distribution; metabolism after incubation of blastoderms of fertilized eggs of White Leghorn hens;

2α-(1-pyridinio)-5α-pregnane-3,20-dione bromide → Progesterone (57-83-0) + dihydroprogesterone (566-65-4) + pregnanedione (128-23-4) + (5S,8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one (65556-93-6) + (5R,8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

Conditions	Yield
With pyridine at 280℃; under 1520 Torr; Product distribution; pyrolysis in GLC vaporizer, various additives (without, 2,4,6-collidine), other temperature (250 deg C);	A 51.5 % Chromat. B 11.9 % Chromat. C 2.2 % Chromat. D 26.4 % Chromat. E 3.1 % Chromat.

1-((8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-ylidene)-pyrrolidinium; perchlorate → dihydroprogesterone (566-65-4) + pregnanedione (128-23-4)

Conditions	Yield
With 1-Benzyl-1,4-dihydronicotinamide; water 1.) acetonitrile, 40 h, reflux 2.) acetonitrile, reflux, 1 h; Multistep reaction. Yields of byproduct given;
With 1-Benzyl-1,4-dihydronicotinamide; water 1.) acetonitrile, 40 h, reflux 2.) acetonitrile, reflux, 1 h; Multistep reaction;

3-hydroxy-pregna-5,16-dion-20-one → dihydroprogesterone (566-65-4)

Conditions	Yield
With palladium on activated charcoal Hydrogenation.anschliessende Oxidation mit CrO3;

isopregnanolone (516-55-2) + acetic acid (64-19-7) + CrO3 → dihydroprogesterone (566-65-4)

dihydroprogesterone (566-65-4) + <2H9>trimethylsulphoxonium iodide (23726-00-3) → 1-((3R,5S,8R,9S,10S,13S,14S,17S)-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-3,2'-oxiran]-17-yl-3',3'-d2)ethan-1-one

Conditions	Yield
Stage #1: <2H9>trimethylsulphoxonium iodide With potassium tert-butylate In dimethylsulfoxide-d6 at 60℃; for 1h; Inert atmosphere; Stage #2: dihydroprogesterone In dimethylsulfoxide-d6 at 20℃;	99%

2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane (7381-30-8) + dihydroprogesterone (566-65-4) → C23H36O3 (98632-74-7)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 6h;	94%

dihydroprogesterone (566-65-4) + trimethylsulfoxonium iodide (1774-47-6) → 1-((2’R,8R,10S,13S,14S,17S)-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-3,2’-oxiran]-17-yl)ethanone (148256-45-5)

Conditions	Yield
Stage #1: trimethylsulfoxonium iodide In dimethyl sulfoxide at 65℃; for 2h; Inert atmosphere; Stage #2: dihydroprogesterone In dimethyl sulfoxide at 20 - 35℃; for 2h; Inert atmosphere;	94%
Stage #1: trimethylsulfoxonium iodide With potassium tert-butylate In dimethyl sulfoxide at 60℃; for 1h; Inert atmosphere; Stage #2: dihydroprogesterone In dimethyl sulfoxide at 20℃;	87%
With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 5h;	75%
With sodium hydride 1.) DMSO, RT, 1 h, 2.) DMSO, 2.5 h; Yield given. Multistep reaction;

dihydroprogesterone (566-65-4) → anti-3-oxime of 5α-pregnane-3,20-dione (6750-73-8)

Conditions	Yield
With pyridine; hydroxylamine hydrochloride at 0℃; for 3h;	92%

dihydroprogesterone (566-65-4) + methylmagnesium chloride (676-58-4) → ganaxolone (38398-32-2)

Conditions	Yield
Stage #1: methylmagnesium chloride With iron(III) chloride; lithium chloride In tetrahydrofuran at -35℃; Stage #2: dihydroprogesterone In tetrahydrofuran at -35 - -18℃; for 3h; Stage #3: With hydrogenchloride; water In tetrahydrofuran at 25℃; Product distribution / selectivity;	91%

dihydroprogesterone (566-65-4) → 2R-(+)-2α-fluoro-5α-pregnane-3,20-dione

Conditions	Yield
With ent-9-amino(9-deoxy)epi-hydroquinine; sodium carbonate; N-fluorobis(benzenesulfon)imide; trichloroacetic acid In tetrahydrofuran; dichloromethane at -10℃; for 48h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	91%

dihydroprogesterone (566-65-4) → allopregnan-20-one (848-62-4)

Conditions	Yield
With zinc In acetic acid at 15℃; for 0.25h; ultrasonic irradiation;	90%
With hydrogenchloride; zinc

methanol (67-56-1) + dihydroprogesterone (566-65-4) → 3,3-dimethoxy-5α-pregnan-20-one (18003-79-7)

Conditions	Yield
With toluene-4-sulfonic acid at 20 - 60℃; for 1h;	90%
With hydrogen; Wilkinson's catalyst
With toluene-4-sulfonic acid Heating;
With toluene-4-sulfonic acid In methanol at 25 - 65℃; for 1h;

dihydroprogesterone (566-65-4) → (5S,6R,8R,9S,10R,13S,14S,17R)-17-Acetyl-2,2,6,17-tetrachloro-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one (185041-91-2)

Conditions	Yield
With manganese(IV) oxide; acetic acid; acetyl chloride Ambient temperature;	90%

dihydroprogesterone (566-65-4) + methylmagnesium bromide (75-16-1) → ganaxolone (38398-32-2)

Conditions	Yield
Stage #1: methylmagnesium bromide With iron(III) chloride; lithium chloride In tetrahydrofuran; diethyl ether at -35 - -30℃; for 0.5h; Stage #2: dihydroprogesterone In tetrahydrofuran; diethyl ether at -20 - -15℃; for 2h;	81%
In toluene at -70℃; for 2h;	0.3 g

dihydroprogesterone (566-65-4) → (5S,8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one (65556-93-6)

Conditions	Yield
With oxygen; palladium diacetate; trifluoroacetic acid In dimethyl sulfoxide at 80℃; for 8h; Sealed tube;	81%

dihydroprogesterone (566-65-4) + ethylmagnesium bromide (925-90-6) → C23H38O2

Conditions	Yield
Stage #1: dihydroprogesterone With 2,4,6-tri-tert-butylphenoxol; trimethylaluminum In toluene at -70 - 0℃; for 1h; Inert atmosphere; Stage #2: ethylmagnesium bromide In diethyl ether; toluene at -70℃; for 1h;	78%

dihydroprogesterone (566-65-4) + (2-nitrophenyl)hydrazine (3034-19-3) → bis-(o.nitro)fenilidrazone del 5α-pregnan-3,20-dione

Conditions	Yield
In ethanol for 0.5h; Heating;	73%

dihydroprogesterone (566-65-4) + acetylenemagnesium bromide (4301-14-8) → UC2003 (178885-91-1) + UC2002 (162883-06-9)

Conditions	Yield
In tetrahydrofuran at 20℃;	A 13% B 72%

dihydroprogesterone (566-65-4) + N-Methyl-N,O-bis(trimethylsilyl)hydroxylamine (22737-33-3) → C22H35NO2 (132734-44-2)

Conditions	Yield
In benzene Heating;	71%

dihydroprogesterone (566-65-4) → isopregnanolone (516-55-2) + tetrahydroprogesterone (516-54-1)

Conditions	Yield
With trimethylamine-borane; silica gel; iron(III) chloride In benzene for 2h; Product distribution; Ambient temperature; various catalysts and times;	A 66.4% B 32.5%
With trimethylamine-borane; silica gel; iron(III) chloride In benzene for 2h; Ambient temperature;	A 66.4% B 32.5%
With ethanol; nickel Hydrogenation;
With morpholine-borane In toluene at 23℃; for 1.5h; Title compound not separated from byproducts;

dihydroprogesterone (566-65-4) + 4-methoxy-aniline (104-94-9) → (5S,8S,9S,10S,13S,14S,17S)-17-acetyl-2-(4-methoxyphenylamino)-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine; trifluorormethanesulfonic acid; oxygen In m-xylene at 130℃; under 760.051 Torr; for 4h; regioselective reaction;	66%

dihydroprogesterone (566-65-4) → tetrahydroprogesterone (516-54-1)

Conditions	Yield
Stage #1: dihydroprogesterone With potassium tri-sec-butyl-borohydride In tetrahydrofuran at -78℃; for 5h; Stage #2: With sodium hydroxide; dihydrogen peroxide at 20℃; for 2h;	63%
With potassium phosphate buffer; 1,4-dihydronicotinamide adenine dinucleotide; NAD:3-α-hydroxy-5α-pregnan-20-one oxidoreductase at 37℃;
With hydrogen bromide; acetic acid; platinum Hydrogenation.unter Erwaermen und Behandlung des Reaktionsprodukts mit methanol. KOH bei Siedetemperatur;

dihydroprogesterone (566-65-4) → tetrahydroprogesterone (516-54-1) + 1-((3R,5S,8R,9S,10S,13S,14S,17R)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanone

Conditions	Yield
With phosphonic Acid; hydrogen hexachloroiridate In water; isopropyl alcohol	A 60% B 12%

dihydroprogesterone (566-65-4) → 2α-bromo-5α-pregnane-3,20-dione (6656-43-5)

Conditions	Yield
With hydrogen bromide; bromine In acetic acid for 0.25h;	57%
With hydrogen bromide; bromine; acetic acid at 20℃;

1-methyl-2(1H)-quinoxalinone (6479-18-1) + dihydroprogesterone (566-65-4) → 3-((E)-2-((5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-1-(hydroxyimino)-2-oxoethyl)-1-methylquinoxalin-2(1H)-one

Conditions	Yield
With tert.-butylnitrite; methanesulfonic acid at 20℃; for 6h;	40%
With tert.-butylnitrite; trifluoroacetic acid In dichloromethane at 20℃; for 6h;	32%

dihydroprogesterone (566-65-4) → C21H33(2)HO2

Conditions	Yield
With sodium borodeuteride; sodium hydroxide In pyridine; methanol; water at 0 - 10℃; for 0.5h; Cooling with ice;	35%

Upstream product

• 145-13-1 1-(3-Hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethanone 
• 57-83-0 Progesterone 
• 145-13-1 Pregnenolone 
• 1778-02-5 Pregnenolone acetate 
• 516-55-2 isopregnanolone 
• 566-56-3 5α-pregnan-3β,20α-diol 
• 516-53-0 (20R)-5α-Pregnandiol-(3β.20) 
• 7680-01-5 3β-methoxy-5α-pregnane-20-one 
• 64-19-7 acetic acid 
• 17652-16-3 pregna-4,9⁽¹¹⁾-diene-3,20-dione 
• 566-58-5 5α-pregnane-3α,20α-diol 
• 62973-43-7 17-bromo-5α-pregnanedione-(3,20) 
• 60-29-7 diethyl ether 
• 13164-11-9 5α-H-pregn-16-ene-3,20-dione 

Downstream Products

• 565-96-8 11α-hydroxy-5β-pregnane-3,20-dione 
• 516-55-2 isopregnanolone 
• 516-54-1 tetrahydroprogesterone 
• 641-85-0 5α-pregnane 
• 566-56-3 5α-pregnan-3β,20α-diol 
• 6170-12-3 5α-pregnanedione-(3,20)-dioxime 
• 566-57-4 5alpha-Pregnane-3a,20b-diol 
• 256955-84-7 3α-hydroxy-21-(1'-imidazolyl)-3β-methoxymethyl-5α-pregnan-20-one 
• 75863-26-2 pregna-1,4,16-triene-3,20-dione 
• 177080-77-2 Co 2-1970 
• 38398-32-2 ganaxolone 
• 76043-46-4 17β-acetoxy-4-oxa-A-homo-5α-androstan-3-one 
• 76043-47-5 17β-(acetyloxy)-3-oxa-A-homo-5α-androstan-4-one 

Relevant articles and documents

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Purification and properties of a NAD: 3α-hydroxy-5α-pregnan-20-one-oxidoreductase from rat liver microsomes

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Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration

A generalized, simple and efficient transfer hydrogenation of unsaturated bonds has been developed using HBPin and various proton reagents as hydrogen sources. The substrates, including alkenes, alkynes, aromatic heterocycles, aldehydes, ketones, imines, azo, nitro, epoxy and nitrile compounds, are all applied to this catalytic system. Various groups, which cannot survive under the Pd/C/H2 combination, are tolerated. The activity of the reactants was studied and the trends are as follows: styrene'diphenylmethanimine'benzaldehyde'azobenzene'nitrobenzene'quinoline'acetophenone'benzonitrile. Substrates bearing two or more different unsaturated bonds were also investigated and transfer hydrogenation occurred with excellent chemoselectivity. Nano-palladium catalyst in situ generated from Pd(OAc)2 and HBPin extremely improved the TH efficiency. Furthermore, chemoselective anti-Markovnikov hydrodeuteration of terminal aromatic olefins was achieved using D2O and HBPin via in situ HD generation and discrimination. (Figure presented.).

COMPOSITIONS AND METHODS FOR TREATING CNS DISORDERS

Described herein are neuroactive steroids of the Formula (I): or a pharmaceutically acceptable salt thereof; wherein (II), A, R1, R2, R3a, R4a, R4b, R5, R7a, and R7b are as defined herein. Such compounds are envisioned, in certain embodiments, to behave as GABA modulators. The present invention also provides pharmaceutical compositions comprising a compound of the present invention and methods of use and treatment, e.g., such for inducing sedation and/or anesthesia.