(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at -3℃; for 2h; | 92.7% |
morpholine
(2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Conditions | Yield |
---|---|
toluene-4-sulfonic acid In water at 20 - 110℃; for 40h; Product distribution / selectivity; Heating / reflux; | 89.7% |
methanesulfonic acid In water at 20 - 110℃; for 40h; Product distribution / selectivity; Heating / reflux; | |
In water for 72h; Product distribution / selectivity; Heating / reflux; |
A
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
B
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 5h; Product distribution / selectivity; Heating / reflux; | A 67.5% B n/a |
pyrrolidine
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Conditions | Yield |
---|---|
In acetonitrile Reflux; | 62.1% |
A
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
B
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
C
1-[(2β, 3α, 5α, 16β, 17β)-2-(4-morpholinyl)-androstan-16-yl-]-1-(2-propenyl)-pyrrolidinium bromide-3,17-diol
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; |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Conditions | Yield |
---|---|
In morpholine; water |
morpholine
(2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol
A
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
C
2α,3α-epoxy-16α-(pyrrolidin-1-yl)-17β-hydroxy-5α-androstan
D
C27H46N2O2
Conditions | Yield |
---|---|
zinc diacetate In water at 20 - 110℃; for 40h; Product distribution / selectivity; Heating / reflux; |
morpholine
(2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol
A
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
B
2α,3α-epoxy-16α-(pyrrolidin-1-yl)-17β-hydroxy-5α-androstan
D
C27H46N2O2
Conditions | Yield |
---|---|
In water at 20 - 110℃; for 40h; Product distribution / selectivity; Heating / reflux; |
morpholine
(2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol
A
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
B
2α,3α-epoxy-16α-(pyrrolidin-1-yl)-17β-hydroxy-5α-androstan
Conditions | Yield |
---|---|
hydrogenchloride In water at 20 - 110℃; for 40h; Product distribution / selectivity; Heating / reflux; | |
toluene-4-sulfonic acid In water at 20 - 110℃; for 40h; Product distribution / selectivity; Heating / reflux; |
morpholine
(2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol
A
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
B
C27H46N2O2
Conditions | Yield |
---|---|
sulfuric acid In water at 20 - 110℃; for 40h; Product distribution / selectivity; Heating / reflux; |
morpholine
(2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol
A
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
C
C27H46N2O2
Conditions | Yield |
---|---|
iron(III) chloride In water at 20 - 110℃; for 40h; Product distribution / selectivity; Heating / reflux; |
5α-androst-2-en-17-one
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Conditions | Yield |
---|---|
Multi-step reaction with 5 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 View Scheme | |
Multi-step reaction with 4 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 View Scheme |
2α,3α-epoxy-5α-androstan-17-one
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Conditions | Yield |
---|---|
Multi-step reaction with 4 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 View Scheme | |
Multi-step reaction with 3 steps 1: iron(III) chloride / water / Reflux 2: copper(ll) bromide / methanol / Reflux 3: acetonitrile / Reflux View Scheme |
3α-hydroxy-2β-(4-morpholinyl)-5α(H)-androstan-17-one
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Conditions | Yield |
---|---|
Multi-step reaction with 3 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 View Scheme | |
Multi-step reaction with 2 steps 1: copper(ll) bromide / methanol / Reflux 2: acetonitrile / Reflux View Scheme |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 8 h / Inert atmosphere; Reflux 2: sodium tetrahydroborate / methanol / 2 h / -3 °C View Scheme |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
4-nitrophenol acetate
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
Conditions | Yield |
---|---|
With triethylamine In 1,2-dichloro-ethane at 80 - 85℃; regioselective reaction; | 94.1% |
N-Acetylimidazole
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
Conditions | Yield |
---|---|
In dichloromethane at 25℃; for 48h; Product distribution / selectivity; | 92% |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
acetic acid
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
Conditions | Yield |
---|---|
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In acetonitrile for 4.5h; Solvent; Reagent/catalyst; Reflux; | 91.4% |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
acetyl chloride
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
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; |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
acetic anhydride
A
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
B
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)-3,17-bis(acetyloxyoxy)androstane
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; |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
acetyl chloride
A
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
B
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)-3,17-bis(acetyloxyoxy)androstane
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; |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
acetyl chloride
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
Conditions | Yield |
---|---|
In dichloromethane |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
acetyl chloride
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)-3,17-bis(acetyloxyoxy)androstane
Conditions | Yield |
---|---|
In dichloromethane |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
acetic anhydride
A
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
B
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)-3,17-bis(acetyloxyoxy)androstane
C
2α,3α-epoxy-16β-(1-pyrrolidinyl)-5α-androstane-17-one
Conditions | Yield |
---|---|
In dichloromethane; water at 20 - 22℃; for 22h; Product distribution / selectivity; |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
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 |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: dichloromethane / 0 - 5 °C / Large scale 2: hydrogenchloride / dichloromethane / 20 - 25 °C / Large scale 3: dichloromethane / 10 °C / Inert atmosphere; Large scale View Scheme |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
acetic anhydride
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)-3,17-bis(acetyloxyoxy)androstane
Conditions | Yield |
---|---|
In dichloromethane at 0 - 5℃; Large scale; | 3.4 kg |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
acetic anhydride
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 25℃; for 22h; |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dichloromethane View Scheme |
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dichloromethane View Scheme |
Product Name: (2b,3a,5a,16b,17b)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Molecular Structure:
Molecular Formula: C27H46N2O3
Molecular Weight: 446.67
Synonyms of (2b,3a,5a,16b,17b)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol (CAS NO.119302-20-4): Androstane-3,17-diol,2-(4-morpholinyl)-16-(1-pyrrolidinyl)-, (2b,3a,5a,16b,17b)- ; 3,17-dihydroxy-2-(4-morpholinyl)-16-(1-pyrroliny)-androstane ; 2,3-Epoxy-1H-cyclopenta[a]phenanthrene,anddrostan-17-ol deriv ; (2β,3ɑ,5ɑ,16ɑ,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)-androstane-3,17-diol
CAS NO: 119302-20-4
Product Categories: INTERMEDIATESOFROCURONIUMBROMIDE
Polar Surface Area: 56.17 Å2
Index of Refraction of (2b,3a,5a,16b,17b)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol (CAS NO.119302-20-4): 1.574
Molar Refractivity: 126.67 cm3
Molar Volume: 383.7 cm3
Surface Tension: 49.5 dyne/cm
Density: 1.163 g/cm3
Flash Point: 295.7 °C
Enthalpy of Vaporization: 97.56 kJ/mol
Boiling Point: 565.4 °C at 760 mmHg
Vapour Pressure of (2b,3a,5a,16b,17b)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol (CAS NO.119302-20-4): 3.88E-15 mmHg at 25 °C
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