(2b,3a,5a,16b,17b)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

Base Information

• Chemical Name: (2b,3a,5a,16b,17b)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
• CAS No.: 119302-20-4
• Molecular Formula: C27H46N2O3
• Molecular Weight: 446.674
• Mol file: 119302-20-4.mol

Synonyms:2b-(4-Morpholinyl)-16b-(1-pyrrolidinyl)-5a-androstane-3a,17b-diol;Androstane-3,17-diol,2-(4-morpholinyl)-16-(1-pyrrolidinyl)-, (2b,3a,5a,16b,17b)-;

Chemical Property of (2b,3a,5a,16b,17b)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

Chemical Property:

• Appearance/Colour: Whitish or yellowish crystalline powder
• Vapor Pressure: 3.88E-15mmHg at 25°C
• Melting Point: 161-169 °C
• Refractive Index: 1.574
• Boiling Point: 565.4 °C at 760 mmHg
• PKA: 14.69±0.70(Predicted)
• Flash Point: 295.7 °C
• PSA: 56.17000
• Density: 1.163 g/cm³
• LogP: 3.01170
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated)

Purity/Quality:

99%min ^*data from raw suppliers

(2β,3α,5α,16β,17β)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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. This compound is used in the synthesis of the neuromuscular blocking agent rocuronium bromide.

Technology Process of (2b,3a,5a,16b,17b)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol

There total 15 articles about (2b,3a,5a,16b,17b)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol 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: 92.7%

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)

Guidance literature:

With sodium tetrahydroborate; In methanol; at -3 ℃; for 2h;

DOI:10.1016/j.cclet.2016.10.026

Reference yield: 89.7%

morpholine (110-91-8,99108-56-2) + (2α,3α,5α,16β,17β)-2,3-epoxy-16-(1-pyrrolidinyl)-androstan-17-ol (119302-19-1) → (2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol (119302-20-4)

Guidance literature:

toluene-4-sulfonic acid; In water; at 20 - 110 ℃; for 40h; Product distribution / selectivity; Heating / reflux;

Reference yield: 67.5%

rocuronium bromide → (2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)-3-hydroxy-17-acetoxyandrostane (119302-24-8) + (2β,3α,5α,16β,17β)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol (119302-20-4)

Guidance literature:

In N,N-dimethyl-formamide; for 5h; Product distribution / selectivity; Heating / reflux;

upstream raw materials:

morpholine

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

5α-androst-2-en-17-one

2α,3α-epoxy-5α-androstan-17-one

Downstream raw materials:

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

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

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

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

Refernces

• 1、 -. "Novel method for preparing rocuronium bromide". . . Retrieved 2017/11/18.
• 2、 -. "Method of reprocessing quaternary ammonium-containing neuromuscular blocking agents". Page/Page column 5; 4. . Retrieved 2008/06/13.