20410-98-4

Basic information

• Product Name: 6a-Naltrexol
• Synonyms: (5α,6α)-17-(CyclopropylMethyl)-4,5-epoxy-Morphinan-3,6,14-triol;6a-Naltrexol;EN 2260;17-(Cyclopropylmethyl)-4,5α-epoxymorphinan-3,6α,14-triol;4,5α-Epoxy-17-(cyclopropylmethyl)morphinan-3,6α,14β-triol;(4R,4aS,7S,7aR,12bS)-3-(cyclopropylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol;6-Naltrexol (CRM)
• CAS NO: 20410-98-4
• Molecular Formula: C₂₀H₂₅NO₄
• Molecular Weight: 343.4168
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 20410-98-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 66-76?C
• Boiling Point: 557.5°Cat760mmHg
• Flash Point: 291°C
• Appearance: /
• Density: 1.48g/cm³
• Vapor Pressure: 2.9E-13mmHg at 25°C
• Refractive Index: 1.719
• Storage Temp.: Refrigerator
• PKA: 9.39±0.60(Predicted)
• CAS DataBase Reference: 6a-Naltrexol(CAS DataBase Reference)
• NIST Chemistry Reference: 6a-Naltrexol(20410-98-4)
• EPA Substance Registry System: 6a-Naltrexol(20410-98-4)

Safety Data

• Hazardous Substances Data: 20410-98-4(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

A metabolite of Naltrexone.

InChI:InChI=1/C20H25NO4/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11/h3-4,11,14-15,18,22-24H,1-2,5-10H2/t14-,15?,18?,19?,20?/m1/s1

Upstream product

• 124154-49-0 3-O-(tert-butyldimethylsilyl)-4,5α-epoxy-3,6α,14-trihydroxy-17-(cyclopropylmethyl)morphinan 
• 7051-34-5 cyclopropylcarbinyl bromide 
• 58477-92-2 14-hydroxydihydronormorphine 
• 33522-95-1 noroxymorphone 
• 1489-69-6 Cyclopropanecarboxaldehyde 
• 67210-64-4 6α,14β-diacetoxy-4,5percenta-epoxy-3-methoxy-17-methyl-morphinan 
• 142641-92-7 C₂₄H₂₇NO₈ 
• 116388-83-1 C₂₂H₂₄N₂O₆ 
• 116499-16-2 beta-Noroxycodol 
• 16676-29-2 naltrexone Hydrochloride 
• 116388-85-3 (5α,6α)-17-(cyclopropylmethyl)-4,5-epoxy-3-methoxymorphinan-6,14-diol 
• 16590-41-3 Naltrexone 

Downstream Products

• 159465-54-0 17-(cyclopropylmethyl)-3-(benzyloxy)-4,5α-epoxy-6α,14-dihydroxymorphinan 
• 159465-60-8 17-(cyclopropylmethyl)-3-(triphenylmethoxy)-6α-(9-anthracylmethoxy)-4,5α-epoxy-14-hydroxymorphinan 
• 159465-56-2 17-(cyclopropylmethyl)-3-(benzyloxy)-6α-(4-biphenylylmethoxy)-4,5α-epoxy-14-hydroxymorphinan 
• 159465-57-3 17-(cyclopropylmethyl)-3-(benzyloxy)-6α-(2-naphthylmethoxy)-4,5α-epoxy-14-hydroxymorphinan 
• 159465-59-5 17-(cyclopropylmethyl)-3-(benzyloxy)-6α-(1-naphthylmethoxy)-4,5α-epoxy-14-hydroxymorphinan 
• 159465-55-1 17-(cyclopropylmethyl)-3,6α-bis(benzyloxy)-4,5α-epoxy-14-hydroxymorphinan 
• 159465-61-9 17-(cyclopropylmethyl)-3-(triphenylmethoxy)-4,5α-epoxy-6α,14-dihydroxymorphinan 

Relevant articles and documents

CONVENIENT PREPARATION OF N-SUBSTITUTED MORPHINAN-6-OLS FROM MORPHINAN-6-ONES

Described herein are methods of preparing 6-hydroxy N-alkyl morphinan-6-ols from morphinan-6-ones, as illustrated below: wherein the variables R1, R2, R3, R10, R11, R14, and are as defined herein and wherein the reactions occur in a one-pot procedure using a boron based reducing agent.

PROCESS FOR REDUCING THE 6-KETO GROUP OF A MORPHINAN ALKALOID TO THE 6-HYDROXY GROUP BY HYDROGENATION

The present invention relates to a process for the reduction of a 6-keto group in a morphinan alkaloid to the corresponding 6-hydroxy group, comprising hydrogenating the 6-keto group using gaseous hydrogen in the presence of a heterogeneous catalyst and a solvent, to yield the 6-hydroxy morphinan alkaloid, wherein the reduction is carried out at a pH in the range of about 5 to about 7, and the 6-hydroxy morphinan alkaloid has an α:β ratio of > 85: 15.

IMPROVED PROCESS FOR THE PREPARATION OF 6-ALPHA-HYDROXY-N-ALKYLATED OPIATES

The present invention is directed to the conversion of a 6-keto morphinan to a 6-alpha-hydroxy morphinan in the presence of a ruthenium, rhodium, or iridium asymmetric catalyst and a hydrogen source.