2a,3a-Epoxy-16b-(1-pyrrolidinyl)-5a-androstan-17b-ol

Base Information

• Chemical Name: 2a,3a-Epoxy-16b-(1-pyrrolidinyl)-5a-androstan-17b-ol
• CAS No.: 119302-19-1
• Molecular Formula: C23H37NO2
• Molecular Weight: 359.552
• European Community (EC) Number: 601-593-4
• UNII: QY44AP6HZH
• DSSTox Substance ID: DTXSID201174294
• Wikidata: Q76507355
• Mol file: 119302-19-1.mol

Synonyms:119302-19-1;2a,3a-Epoxy-16b-(1-pyrrolidinyl)-5a-androstan-17b-ol;QY44AP6HZH;UNII-QY44AP6HZH;EC 601-593-4;2alpha,3alpha-epoxy-16beta-(1-pyrrolidinyl)-5alpha-androstan-17beta-ol;2,3-Epoxy-1H-cyclopenta(a)phenanthrene,androstan-17-ol;2,3-Epoxy-1H-cyclopenta[a]phenanthrene,androstan-17-ol;(2a,3a,5a,16b,17b)-2,3-Epoxy-16-(1-pyrrolidinyl)androstan-17-ol;(2alpha,3alpha,5alpha,16beta,17beta)-2,3-epoxy-16-(1-pyrrolidinyl)androstan-17-ol;(1S,2S,4R,6S,8S,11R,12S,14S,15R,16S)-2,16-dimethyl-14-pyrrolidin-1-yl-5-oxapentacyclo[9.7.0.02,8.04,6.012,16]octadecan-15-ol;Androstan-17-ol, 2,3-epoxy-16-(1-pyrrolidinyl)-, (2alpha,3alpha,5alpha,16beta,17beta)-;Androstan-17-ol, 2,3-epoxy-16-(1-pyrrolidinyl)-, (2a,3a,5a,16b,17b)-;ROCURONIUM IMPURITY 2;SCHEMBL3837726;OPYVYACKKDTREB-NXECLLCESA-N;DTXSID201174294;AKOS015896060;AC-5925;A848323;2alpha,3alpha-epoxy-16beta-(1-pyrrolidinyl)-5alpha-androstane-17beta-ol;Androstan-17-ol, 2,3-epoxy-16-(1-pyrrolidinyl)-, (2,3,5,16,17)-;(2alpha,3alpha,5alpha,16beta,17beta)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol;(2alpha,3alpha,5alpha,16beta,17beta)2,3-epoxy-16-(1-pyrrolidinyl )-androstan-17-ol;(2alpha,3alpha,5alpha,16beta,17beta)2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol;2.ALPHA.,3.ALPHA.-EPOXY-16.BETA.-(1-PYRROLIDINYL)-5.ALPHA.-ANDROSTAN-17.BETA.-OL;(2.ALPHA.,3.ALPHA.,5.ALPHA.,16.BETA.,17.BETA.)-2,3-EPOXY-16-(1-PYRROLIDINYL)ANDROSTAN-17-OL;ANDROSTAN-17-OL, 2,3-EPOXY-16-(1-PYRROLIDINYL)-, (2.ALPHA.,3.ALPHA.,5.ALPHA.,16.BETA.,17.BETA.)-

Chemical Property of 2a,3a-Epoxy-16b-(1-pyrrolidinyl)-5a-androstan-17b-ol

Chemical Property:

• Vapor Pressure: 8.59E-11mmHg at 25°C
• Refractive Index: 1.569
• Boiling Point: 469.613 °C at 760 mmHg
• PKA: 14.73±0.70(Predicted)
• Flash Point: 237.814 °C
• PSA: 36.00000
• Density: 1.144 g/cm³
• LogP: 3.77950
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 359.282429423
• Heavy Atom Count: 26
• Complexity: 589

Purity/Quality:

99% ^*data from raw suppliers

2a,3a-Epoxy-16b-(1-pyrrolidinyl)-5a-androstan-17b-ol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CC(C2O)N4CCCC4)CCC5C3(CC6C(C5)O6)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@@H]([C@@H]2O)N4CCCC4)CC[C@@H]5[C@@]3(C[C@@H]6[C@H](C5)O6)C
• Uses: (2a,3a,5a,16b,17b)-2,3-Epoxy-16-(1-pyrrolidinyl)androstan-17-ol is used in the synthesis of rocuronium bromide (R639500), which acts as a neuromuscular blocking agent.

Technology Process of 2a,3a-Epoxy-16b-(1-pyrrolidinyl)-5a-androstan-17b-ol

There total 4 articles about 2a,3a-Epoxy-16b-(1-pyrrolidinyl)-5a-androstan-17b-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.3%

2α,3α-epoxy-16β-(1-pyrrolidinyl)-5α-androstane-17-one (159325-45-8) → (2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol (119302-19-1)

Guidance literature:

2α,3α-epoxy-16β-(1-pyrrolidinyl)-5α-androstane-17-one; With sodium tetrahydroborate; In methanol; at -10 - 24 ℃; for 3h;

With water; In methanol; dichloromethane; at 20 - 22 ℃; for 0.166667h; Product distribution / selectivity;

Reference yield:

pyrrolidine (123-75-1) + (2α,3α,5α,16β,17α)-2,3,16,17-bisepoxy-androstan-17-ol acetate → (2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol (119302-19-1)

Guidance literature:

With sodium hydroxide; sodium borohydrid; In methanol; dichloromethane; water; acetone;

Reference yield:

2α,3α-epoxy-16β-(1-pyrrolidinyl)-5α-androstane-17-one (159325-45-8) → (2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol (119302-19-1) + C27H46N2O2 (144209-33-6)

Guidance literature:

2α,3α-epoxy-16β-(1-pyrrolidinyl)-5α-androstane-17-one; With sodium tetrahydroborate; In methanol; dichloromethane; at 0 - 25 ℃; for 2.66667h;

With water; In methanol; at 25 ℃; for 1h; Product distribution / selectivity;

upstream raw materials:

pyrrolidine

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

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

Downstream raw materials:

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

C₂₇H₄₆N₂O₂

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

Refernces

• 1、 -. "Androstane derivatives substituted by a quaternary ammonium group in 16-position, pharmaceutical compositions containing them and process for preparing same". . . Retrieved 2008/06/13.
• 2、 -. "Novel 2β-morpholino-androstane derivatives". . . Retrieved 2008/06/13.