(2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane supplier

Name
(2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
EINECS 425-650-6
CAS No. 119302-24-8
Article Data10
CAS DataBase
Density 1.17 g/cm³
Solubility
Melting Point
Formula C₂₉H₄₈N₂O₄
Boiling Point 574.1 °C at 760 mmHg
Molecular Weight 488.711
Flash Point 301 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2b-(4-Morpholinyl)-16b-(1-pyrrolidinyl)-5a-androstane-3a,17b-diol 17-acetate;Org 20860;Androstane-3,17-diol,2-(4-morpholinyl)-16-(1-pyrrolidinyl)-, 17-acetate, (2b,3a,5a,16b,17b)-;
PSA 62.24000
LogP 3.58250

Synthetic route

: 119302-20-4
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

: 830-03-5
4-nitrophenol acetate

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
With triethylamine In 1,2-dichloro-ethane at 80 - 85℃; regioselective reaction;	94.1%

: 2466-76-4
N-Acetylimidazole

: 119302-20-4
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
In dichloromethane at 25℃; for 48h; Product distribution / selectivity;	92%

: 119302-20-4
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

: 64-19-7
acetic acid

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In acetonitrile for 4.5h; Solvent; Reagent/catalyst; Reflux;	91.4%

: 119302-20-4
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

: 75-36-5
acetyl chloride

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
In dichloromethane at 20 - 25℃;	89.7%
In dichloromethane at 35℃; for 4h;
Stage #1: (2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol; acetyl chloride In dichloromethane at 20℃; for 18h; Stage #2: With sodium carbonate In dichloromethane; water Product distribution / selectivity;

: rocuronium bromide

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
at 150℃; for 10h; Product distribution / selectivity; vacuum;	81%
In isopropyl alcohol for 6h; Product distribution / selectivity; Heating / reflux;
In diethylamine for 6h; Product distribution / selectivity; Heating / reflux;
In (methyl)isobutyl ketone for 6h; Product distribution / selectivity; Heating / reflux;
In dimethyl sulfoxide for 6h; Product distribution / selectivity; Heating / reflux;

: 119302-20-4
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

: 108-24-7
acetic anhydride

A: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

B: 119302-22-6
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)-3,17-bis(acetyloxyoxy)androstane

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20 - 22℃; for 22h; Product distribution / selectivity;	A 68.8% B n/a
In acetonitrile for 1h; Product distribution / selectivity; Heating / reflux;	A 53.4 - 96.1 %Chromat. B 0.2 - 39.5 %Chromat.
With pyridine In dichloromethane at 20 - 22℃; for 22h; Product distribution / selectivity;

...Expand

: rocuronium bromide

A: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

B: 119302-20-4
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 5h; Product distribution / selectivity; Heating / reflux;	A 67.5% B n/a

: 119302-22-6
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)-3,17-bis(acetyloxyoxy)androstane

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
With hydrogenchloride In dichloromethane at 20 - 25℃; Large scale;	0.35%

: 119302-20-4
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

: 75-36-5
acetyl chloride

A: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

B: 119302-22-6
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)-3,17-bis(acetyloxyoxy)androstane

Conditions

Conditions	Yield
In dichloromethane at 0 - 40℃; for 18h; Product distribution / selectivity;	A 56.7 - 67.2 %Chromat. B 6.2 - 21.7 %Chromat.
In dichloromethane at 23℃; for 24h; Product distribution / selectivity;	A 94.1 %Chromat. B 2.1 %Chromat.
With triethylamine In dichloromethane at 20 - 22℃; for 22h; Product distribution / selectivity;
Stage #1: (2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol; acetyl chloride In dichloromethane at 20℃; for 29h; Stage #2: With sodium carbonate In dichloromethane; water Product distribution / selectivity;

...Expand

: rocuronium bromide

A: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

B: 119302-20-4
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

C: 119302-86-2
1-[(2β, 3α, 5α, 16β, 17β)-2-(4-morpholinyl)-androstan-16-yl-]-1-(2-propenyl)-pyrrolidinium bromide-3,17-diol

Conditions

Conditions	Yield
In dimethyl acetamide (DMA) for 3h; Product distribution / selectivity; Heating / reflux;
sodium thiophenolate In isopropyl alcohol for 4h; Product distribution / selectivity; Heating / reflux;
In N,N-dimethyl-formamide for 5h; Product distribution / selectivity; Heating / reflux;

...Expand

: rocuronium bromide

A: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

B: 119302-86-2
1-[(2β, 3α, 5α, 16β, 17β)-2-(4-morpholinyl)-androstan-16-yl-]-1-(2-propenyl)-pyrrolidinium bromide-3,17-diol

Conditions

Conditions	Yield
In 2,4-dimethylpentan-3-one for 16h; Product distribution / selectivity; Heating / reflux;
sodium thiophenolate In 2,4-dimethylpentan-3-one at 70℃; for 5h; Product distribution / selectivity;

diethyl ether-n-hexane: diethyl ether-n-hexane

: 119302-20-4
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

: 75-36-5
acetyl chloride

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
In dichloromethane

...Expand

: 119302-20-4
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

: 108-24-7
acetic anhydride

A: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

B: 119302-22-6
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)-3,17-bis(acetyloxyoxy)androstane

C: 159325-45-8
2α,3α-epoxy-16β-(1-pyrrolidinyl)-5α-androstane-17-one

Conditions

Conditions	Yield
In dichloromethane; water at 20 - 22℃; for 22h; Product distribution / selectivity;

...Expand

: 119302-20-4
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 0 - 5 °C / Large scale 2: hydrogenchloride / dichloromethane / 20 - 25 °C / Large scale View Scheme

: 3α-hydroxy-2β-(4-morpholinyl)-16β-(1-pyrrolidinyl)-5α-androstan-17-one

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 2 h / -3 °C 2: triethylamine / dichloromethane / 22 h / 25 °C View Scheme

: 119302-20-4
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

: 108-24-7
acetic anhydride

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 25℃; for 22h;

: 14639-79-3, 24174-20-7, 82467-84-3, 963-75-7
5α-androst-2-en-17-one

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: dihydrogen peroxide; formic acid / dichloromethane / 5 h / 20 °C 2.1: iron(III) chloride / water / 0.5 h / 20 °C 2.2: 24 h / 130 °C 3.1: copper(ll) bromide / methanol / 30 h / 70 °C / Inert atmosphere 4.1: acetonitrile / 8 h / Inert atmosphere; Reflux 5.1: sodium tetrahydroborate / methanol / 2 h / -3 °C 6.1: triethylamine / dichloromethane / 22 h / 25 °C View Scheme
Multi-step reaction with 5 steps 1: 3-chloro-benzenecarboperoxoic acid / chloroform / 0 - 5 °C 2: iron(III) chloride / water / Reflux 3: copper(ll) bromide / methanol / Reflux 4: acetonitrile / Reflux 5: dichloromethane / 20 - 25 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: dihydrogen peroxide; formic acid / dichloromethane / 5 h / 20 °C
2.1: iron(III) chloride / water / 0.5 h / 20 °C
2.2: 24 h / 130 °C
3.1: copper(ll) bromide / methanol / 30 h / 70 °C / Inert atmosphere
4.1: acetonitrile / 8 h / Inert atmosphere; Reflux
5.1: sodium tetrahydroborate / methanol / 2 h / -3 °C
6.1: triethylamine / dichloromethane / 22 h / 25 °C
View Scheme

Multi-step reaction with 5 steps
1: 3-chloro-benzenecarboperoxoic acid / chloroform / 0 - 5 °C
2: iron(III) chloride / water / Reflux
3: copper(ll) bromide / methanol / Reflux
4: acetonitrile / Reflux
5: dichloromethane / 20 - 25 °C
View Scheme

: 965-67-3, 7676-05-3, 13094-19-4
2α,3α-epoxy-5α-androstan-17-one

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: iron(III) chloride / water / 0.5 h / 20 °C 1.2: 24 h / 130 °C 2.1: copper(ll) bromide / methanol / 30 h / 70 °C / Inert atmosphere 3.1: acetonitrile / 8 h / Inert atmosphere; Reflux 4.1: sodium tetrahydroborate / methanol / 2 h / -3 °C 5.1: triethylamine / dichloromethane / 22 h / 25 °C View Scheme
Multi-step reaction with 4 steps 1: iron(III) chloride / water / Reflux 2: copper(ll) bromide / methanol / Reflux 3: acetonitrile / Reflux 4: dichloromethane / 20 - 25 °C View Scheme

: 52-72-2
3α-hydroxy-2β-(4-morpholinyl)-5α(H)-androstan-17-one

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: copper(ll) bromide / methanol / 30 h / 70 °C / Inert atmosphere 2: acetonitrile / 8 h / Inert atmosphere; Reflux 3: sodium tetrahydroborate / methanol / 2 h / -3 °C 4: triethylamine / dichloromethane / 22 h / 25 °C View Scheme
Multi-step reaction with 3 steps 1: copper(ll) bromide / methanol / Reflux 2: acetonitrile / Reflux 3: dichloromethane / 20 - 25 °C View Scheme

: 3α-hydroxy-2β-(4-morpholinyl)-16α-bromo-5α-androstan-17-one

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetonitrile / 8 h / Inert atmosphere; Reflux 2: sodium tetrahydroborate / methanol / 2 h / -3 °C 3: triethylamine / dichloromethane / 22 h / 25 °C View Scheme

: 2β-(4-morpholinyl)-3α-ol-16β-bromo-17-one-5α-androstane

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: dichloromethane / 20 - 25 °C View Scheme

: (2α,3α,5α,16β,17β)2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: morpholine; water 2: dichloromethane View Scheme

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

A: 1190105-65-7
Br(1-)*C32H53N2O3(1+)

B: Br(1-)*C34H55N2O5(1+)

C: rocuronium bromide

Conditions

Conditions	Yield
Stage #1: allyl bromide With sodium carbonate In dichloromethane at 20℃; for 0.5h; Stage #2: (2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)-3-hydroxy-17-acetoxyandrostane In dichloromethane at 40℃; for 22h; Product distribution / selectivity;	A n/a B n/a C 100%

...Expand

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

: 106-95-6
allyl bromide

: rocuronium bromide

Conditions

Conditions	Yield
With aluminum oxide In isopropyl alcohol at 25 - 30℃; for 6h; Reagent/catalyst; Solvent; Time;	96.1%
With sodium carbonate In dichloromethane at 20 - 30℃;	95.2%
In acetonitrile at 20℃; for 3h;	93.7%

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

: C29H46N2O4

Conditions

Conditions	Yield
Stage #1: (2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)-3-hydroxy-17-acetoxyandrostane With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -60℃; for 0.25h; Stage #2: With triethylamine In dichloromethane at -78℃; for 0.5h; Temperature;	60%

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

: 106-95-6
allyl bromide

: rocuronium bromide

Conditions

Conditions	Yield
In dichloromethane

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

: 1-[(2β,3α,5α,16β,17β)-17-acetyloxy-3-hydroxy-2-(4-morpholinyl)-androstan-16-yl]-1-methylpyrrolidinium bromide

: 119302-24-8
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

A: 1190105-66-8
Br(1-)*C34H55N2O4(1+)

B: rocuronium bromide

Conditions

Conditions	Yield
Stage #1: allyl bromide With sodium carbonate In acetone at 20℃; for 0.5h; Stage #2: (2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)-3-hydroxy-17-acetoxyandrostane In acetone at 40℃; for 22h; Product distribution / selectivity;

(2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane Chemical Properties

Product Name: (2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
Molecular Structure:

Molecular Formula: C₂₉H₄₈N₂O₄
Molecular Weight: 488.7024
Synonyms of (2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane (CAS NO.119302-24-8): 2ss-(4-Morpholinyl)-16ss-(1-pyrrolidinyl)-5a-androstane-3a,17ss-diol 17-acetate ; 2-β-(4-Morpholinyl)-16β-(1-pyrrolidinyl)-5a-androstan-3a,17β-diol-17-acetate ; (2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane ; (2，3，5，16，17)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane;(2b,3a,5a,16b,17b)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)-androstane-3,17-diol 17-acetate
CAS NO: 119302-24-8
Polar Surface Area (2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane (CAS NO.119302-24-8): 51.24 Å²
Index of Refraction: 1.573
Molar Refractivity: 136.81 cm³
Molar Volume: 414.8 cm³
Surface Tension: 50.6 dyne/cm
Density: 1.17 g/cm³
Flash Point: 301 °C
Enthalpy of Vaporization: 98.78 kJ/mol
Boiling Point: 574.1 °C at 760 mmHg
Vapour Pressure (2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane (CAS NO.119302-24-8): 1.44E-15 mmHg at 25 °C

Product Name

(2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane

Synthetic route

(2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane Chemical Properties

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