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| | (2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane Basic information |
| Product Name: | (2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane | | Synonyms: | 2-β-(4-Morpholinyl)-16β-(1-pyrrolidinyl)-5a-androstan-3a,17β-diol-17-acetate;(2B,3A,5A,16B,17B)-17-ACETOXY-3-HYDROXY-2-(4-MORPHOLINYL)-16-(1-PYRROLIDINYL)ANDROSTANE;（2，3，5，16，17）-17-acetoxy-3-hydroxy-2-（4-morpholinyl）-16-（1-pyrrolidinyl）androstane;(2b,3a,5a,16b,17b)-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)-androstane-3,17-diol 17-acetate;2β-(4-Morpholinyl)-16β-(1-pyrrolidinyl)-5α-androstane-3α,17β-diol 17-acetate;2beta-(4-Morpholinyl)-16beta-(1-pyrrolidinyl)-5alpha-androstane-3alpha,17beta-diol 17-acetate;(2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-Morpholinyl)-16-(1-pyrrolidinyl)androstane (2b,3a,5a,16b,17b)-1;RocuroniuM BroMide InterMediate VIII | | CAS: | 119302-24-8 | | MF: | C29H48N2O4 | | MW: | 488.7 | | EINECS: | 601-596-0 | | Product Categories: | Intermediates | | Mol File: | 119302-24-8.mol |  |
| | (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 Preparation Products And Raw materials |
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