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119302-24-8

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  • High quality (2B,3A,5A,16B,17B)-17-Acetoxy-3-Hydroxy-2-(4-Morpholinyl)-16-(1-Pyrrolidinyl)Androstane supplier in China

    Cas No: 119302-24-8

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  • (2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane CAS NO.119302-24-8

    Cas No: 119302-24-8

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  • 2β-(4-Morpholinyl)-16β-(1-pyrrolidinyl)-5α-androstan-3α,17β-diol-17-acetate

    Cas No: 119302-24-8

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119302-24-8 Usage

Uses

(2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane is used in the synthesis of the neuromuscular blocking agent rocuronium bromide.

Check Digit Verification of cas no

The CAS Registry Mumber 119302-24-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,9,3,0 and 2 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 119302-24:
(8*1)+(7*1)+(6*9)+(5*3)+(4*0)+(3*2)+(2*2)+(1*4)=98
98 % 10 = 8
So 119302-24-8 is a valid CAS Registry Number.
InChI:InChI=1/C29H48N2O4/c1-19(32)35-27-24(30-10-4-5-11-30)17-23-21-7-6-20-16-26(33)25(31-12-14-34-15-13-31)18-29(20,3)22(21)8-9-28(23,27)2/h20-27,33H,4-18H2,1-3H3/t20-,21+,22-,23-,24-,25-,26-,27-,28-,29-/m0/s1

119302-24-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

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

1.2 Other means of identification

Product number -
Other names RocuroniuM BroMide InterMediate VIII

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:119302-24-8 SDS

119302-24-8Synthetic route

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

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

4-nitrophenol acetate
830-03-5

4-nitrophenol acetate

(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
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%
N-Acetylimidazole
2466-76-4

N-Acetylimidazole

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

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

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

acetic acid
64-19-7

acetic acid

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

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

acetyl chloride
75-36-5

acetyl chloride

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

rocuronium bromide

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

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

acetic anhydride
108-24-7

acetic anhydride

A

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

(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
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

rocuronium bromide

A

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

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

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

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

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

acetyl chloride
75-36-5

acetyl chloride

A

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

(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
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

rocuronium bromide

A

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

(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
119302-20-4

(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
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;
rocuronium bromide

rocuronium bromide

A

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

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

B

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

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

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

acetyl chloride
75-36-5

acetyl chloride

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

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

Conditions
ConditionsYield
In dichloromethane
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
119302-20-4

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

acetic anhydride
108-24-7

acetic anhydride

A

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

(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
119302-22-6

(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
159325-45-8

2α,3α-epoxy-16β-(1-pyrrolidinyl)-5α-androstane-17-one

Conditions
ConditionsYield
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
119302-20-4

(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
119302-24-8

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

Conditions
ConditionsYield
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

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

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol / 2 h / -3 °C
2: triethylamine / dichloromethane / 22 h / 25 °C
View Scheme
(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
119302-20-4

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

acetic anhydride
108-24-7

acetic anhydride

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

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

Conditions
ConditionsYield
With triethylamine In dichloromethane at 25℃; for 22h;
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
119302-24-8

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

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

2α,3α-epoxy-5α-androstan-17-one

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

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

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

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

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

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

Conditions
ConditionsYield
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

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

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

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

Conditions
ConditionsYield
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

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

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

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

Conditions
ConditionsYield
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

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

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: morpholine; water
2: dichloromethane
View Scheme
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
119302-24-8

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

A

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

Br(1-)*C32H53N2O3(1+)

B

Br(1-)*C34H55N2O5(1+)

Br(1-)*C34H55N2O5(1+)

C

rocuronium bromide

rocuronium bromide

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

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

allyl bromide
106-95-6

allyl bromide

rocuronium bromide

rocuronium bromide

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

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

C29H46N2O4

C29H46N2O4

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

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

allyl bromide
106-95-6

allyl bromide

rocuronium bromide

rocuronium bromide

Conditions
ConditionsYield
In dichloromethane
(2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane
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

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

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

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

A

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

Br(1-)*C34H55N2O4(1+)

B

rocuronium bromide

rocuronium bromide

Conditions
ConditionsYield
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;

119302-24-8Relevant articles and documents

Preparation method of rocuronium bromide intermediate and rocuronium bromide

-

Paragraph 0014; 0041-0042; 0044-0045; 0047-0048; 0050-0051, (2020/03/06)

The invention discloses a preparation method of a rocuronium bromide intermediate and rocuronium bromide. According to the method, (2beta,3alpha,5alpha,16beta,17beta)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol is used as an initial raw material, and is subjected to selective acetylation with glacial acetic acid under the action of a condensing agent to obtain (2beta,3alpha,5alpha,16beta,17beta)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol-17-acetate, and then (2beta,3alpha,5alpha,16beta,17beta)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol-17-acetate issubjected to salt formation with 3-bromopropene in a protic solvent under the action of a basic catalyst to obtain rocuronium bromide. The preparation method adopted in the invention is mild in reaction conditions, simple in post-treatment, and suitable for large-scale industrial application.

A new and efficient method for the synthesis of rocuronium bromide

Wu, Xue-Ying,Wang, Yao-Ling,Hai, Li,Gong, Ping,Wu, Yong

, p. 487 - 492 (2017/01/28)

Rocuronium bromide has been used as an aminosteroid non-depolarizing neuromuscular blocker and muscle relaxant. In this work, a new and efficient route for preparing a key intermediate 2β-(4-morpholinyl)-16β-(1-pyrrolidinyl)-5α-androstan-3α,17β-diol (6) was developed through a ring-opening of epoxide followed by introducing and pyrrolidine. Compound 6 can easily provide rocuronium bromide and the overall yield of compound 6 in 5 steps increased to 57.8%, which was higher than currently reported methods. Extraordinarily, this method would avoid the generation of disubstituted impurities E and F which are difficult to remove.

NOVEL METHOD FOR SYNTHESIS OF NEUROMUSCULAR BLOCKING AGENTS

-

Page/Page column 12, (2016/03/13)

The invention discloses a novel method for preparing neuromuscular blocking agents using aryl esters as a reagent of di-acylation as well as highly regioselective mono-acylation of androstane-diols.

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