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119302-20-4

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Product FOB Price Min.Order Supply Ability Supplier
Androstane-3,17-diol,119302-20-4
Cas No: 119302-20-4
USD $ 600.0-600.0 / Gram 1 Gram 5 Kilogram/Month Wuhan MoonZY Biological Technology Co.,Ltd Contact Supplier
High purity Various Specifications (2b,3a,5a,16b,17b)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol CAS:119302-20-4
Cas No: 119302-20-4
USD $ 100.0-500.0 / Gram 1 Gram 99999 Gram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
High quality 3,17-Dihydroxy-2-(4-Morpholinyl)-16-(1-Pyrrolinyl)-Androstane supplier in China
Cas No: 119302-20-4
No Data No Data Metric Ton/Day Simagchem Corporation Contact Supplier
(2β,3α,5α,16β,17β)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)-androstane-3,17-diol
Cas No: 119302-20-4
No Data No Data No Data Chemwill Asia Co., Ltd. Contact Supplier
(2b,3a,5a,16b,17b)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Cas No: 119302-20-4
No Data 1 Kilogram 20 Metric Ton/Month Henan Allgreen Chemical Co.,Ltd Contact Supplier
Factory Supply (1R,2S,10R,11S,15S)-2,15-dimethyl-4-(morpholin-4-yl)-13-(pyrrolidin-1-yl)tetracyclo[8.7.0.02,?.011,1?]heptadecane-5,14-diol
Cas No: 119302-20-4
No Data 1 1 Ality Chemical Corporation Contact Supplier
(2β,3α,5α,16β,17β)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Cas No: 119302-20-4
No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier
2-(4-morpholinyl)-16-(1-pyrrolidinyl)-5-androstane-3,17-diol
Cas No: 119302-20-4
USD $ 2.0-2.0 / Kilogram 1 Kilogram 1-10 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
(2b,3a,5a,16b,17b)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Cas No: 119302-20-4
USD $ 1.0-2.0 / Metric Ton 1 Metric Ton 500 Metric Ton/Week Hebei yanxi chemical co.,LTD. Contact Supplier
(2b,3a,5a,16b,17b)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
Cas No: 119302-20-4
No Data 1 Kilogram 10 Metric Ton/Month Henan Tianfu Chemical Co., Ltd. Contact Supplier

119302-20-4 Usage

Uses

(2β,3α,5α,16β,17β)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol is used in the synthesis of the neuromuscular blocking agent rocuronium bromide.

Chemical Properties

White Solid
InChI:InChI=1/C27H46N2O3/c1-26-8-7-20-19(21(26)16-22(25(26)31)28-9-3-4-10-28)6-5-18-15-24(30)23(17-27(18,20)2)29-11-13-32-14-12-29/h18-25,30-31H,3-17H2,1-2H3/t18-,19+,20-,21-,22-,23-,24-,25-,26-,27-/m0/s1

119302-20-4SDS

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)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

1.2 Other means of identification

Product number -
Other names 2-(4-MORPHOLINYL)-16-(1-PYRROLIDINYL)-5-ANDROSTANE-3,17-DIOL

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:119302-20-4 SDS

119302-20-4Synthetic route

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)-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
With sodium tetrahydroborate In methanol at -3℃; for 2h;92.7%
morpholine
110-91-8

morpholine

(2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol
119302-19-1

(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
119302-20-4

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

Conditions
ConditionsYield
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;
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
pyrrolidine
123-75-1

pyrrolidine

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)-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 acetonitrile Reflux;62.1%
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;
(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)-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 morpholine; water
morpholine
110-91-8

morpholine

(2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol
119302-19-1

(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
119302-20-4

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

B

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

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

C

2α,3α-epoxy-16α-(pyrrolidin-1-yl)-17β-hydroxy-5α-androstan
930092-98-1

2α,3α-epoxy-16α-(pyrrolidin-1-yl)-17β-hydroxy-5α-androstan

D

C27H46N2O2
144209-33-6

C27H46N2O2

Conditions
ConditionsYield
zinc diacetate In water at 20 - 110℃; for 40h; Product distribution / selectivity; Heating / reflux;
morpholine
110-91-8

morpholine

(2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol
119302-19-1

(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
119302-20-4

(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
930092-98-1

2α,3α-epoxy-16α-(pyrrolidin-1-yl)-17β-hydroxy-5α-androstan

C

C23H39NO3

C23H39NO3

D

C27H46N2O2
144209-33-6

C27H46N2O2

Conditions
ConditionsYield
In water at 20 - 110℃; for 40h; Product distribution / selectivity; Heating / reflux;
morpholine
110-91-8

morpholine

(2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol
119302-19-1

(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
119302-20-4

(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
930092-98-1

2α,3α-epoxy-16α-(pyrrolidin-1-yl)-17β-hydroxy-5α-androstan

C

C23H39NO3

C23H39NO3

Conditions
ConditionsYield
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
110-91-8

morpholine

(2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol
119302-19-1

(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
119302-20-4

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

B

C27H46N2O2
144209-33-6

C27H46N2O2

Conditions
ConditionsYield
sulfuric acid In water at 20 - 110℃; for 40h; Product distribution / selectivity; Heating / reflux;
morpholine
110-91-8

morpholine

(2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol
119302-19-1

(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
119302-20-4

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

B

C23H39NO3

C23H39NO3

C

C27H46N2O2
144209-33-6

C27H46N2O2

Conditions
ConditionsYield
iron(III) chloride In water at 20 - 110℃; for 40h; 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

Conditions
ConditionsYield
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
965-67-3, 7676-05-3, 13094-19-4

2α,3α-epoxy-5α-androstan-17-one

(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
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
52-72-2

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
119302-20-4

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

Conditions
ConditionsYield
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
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)-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
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
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;
(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;
(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;
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

acetyl chloride
75-36-5

acetyl chloride

(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
(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
(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

rocuronium bromide

rocuronium bromide

Conditions
ConditionsYield
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
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)-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 - 5℃; Large scale;3.4 kg
(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)-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

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

Conditions
ConditionsYield
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
119302-20-4

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

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane
View Scheme
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