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(2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
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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 Density 1.17 g/cm3
PSA 62.24000 LogP 3.58250
Solubility N/A Melting Point N/A
Formula C29H48N2O4 Boiling Point 574.1 °C at 760 mmHg
Molecular Weight 488.711 Flash Point 301 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 119302-24-8 ((2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane) Hazard Symbols N/A
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)-;

Article Data 10

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

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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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;

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
ConditionsYield
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;

(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

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