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

Melting point:

152-156°C

Boiling point:

574.1±50.0 °C(Predicted)

Density 

1.17

vapor pressure 

0Pa at 25℃

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly, Heated), Methanol (Slightly)

form 

Solid

pka

14.85±0.70(Predicted)

color 

White to Light Brown

InChIKey

YBZSVMDKHBRYNB-MRKRSBMYNA-N

SMILES

[C@]12(C)CC[C@]3([C@@]([H])(CC[C@@]4([H])C[C@H](O)[C@@H](N5CCOCC5)C[C@]34C)[C@]1([H])C[C@H](N1CCCC1)[C@@H]2OC(C)=O)[H] |&1:0,4,5,9,12,14,22,24,27,33,r|

LogP

3.9 at 22℃ and pH12

(2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane Usage And Synthesis

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.

Synthesis

GENERAL STEPS: To a dry and clean four-necked round-bottomed flask were added (2b,3a,5a,16b,17b)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol (50.0 g), triethylamine (47.58 mL), 4-nitrophenyl acetate (91.04 g) and dichloromethane (500 mL). The reaction mixture was heated to 80-85 °C and maintained under HPLC monitoring for 7-8 h. HPLC analysis showed that the reaction mixture contained 94-95% 17-monoacetate, 5-6% diacetate and 0.2-0.3% 3,17-diol. Upon completion of the reaction, the reaction mixture was quenched with water, followed by post-processing to isolate (2b,3a,5a,16b,17b)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane. The yield was 51.3 g (94.1% yield) and the HPLC purity was as follows: greater than 98% for 17-monoacetate and no more than 2.0% for diacetate. Further purification by acetonitrile crystallization gave the target product with purity greater than 99.5%.

References

[1] Patent: WO2016/9442, 2016, A1. Location in patent: Page/Page column 12

(2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane(119302-24-8)Related Product Information

• Moroxydine hydrochloride
• Rocuronium bromide
• (2b,3a,5a,16b,17b)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol
• 2-Pyrrolidinyl-3-acetyl Desmorpholinylrocuronium Bromide
• (5S,8R,9S,10S,13S,14S)-10,13-dimethyl-1,5,6,7,8,9,10,11,12,13,15,16-dodecahydro-4H-cyclopenta[a]phenanthren-17(14H)-one
• RocuroniuM BroMide IMpurity 15
• Tridemorph
• Dimethomorph
• CHLOROPHOSPHONAZO III
• Moroxydine
• 5a-Androstane-3a,17b-diol
• rocuronium
• N-CETYLMORPHOLINE
• (2β,3α,5α,16β,17β)-17-Acetoxy-3-hydroxy-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane
• Acetoxy