6-Keto Nalbuphine

Base Information

• Chemical Name: 6-Keto Nalbuphine
• CAS No.: 16676-33-8
• Molecular Formula: C21H25 N O4
• Molecular Weight: 355.434
• Mol file: 16676-33-8.mol

Synonyms:Morphinan-6-one,17-(cyclobutylmethyl)-4,5a-epoxy-3,14-dihydroxy- (8CI); 6-Deoxy-6-oxonalbuphine; 6-Ketonalbuphine;EN 1655; N-(Cyclobutylmethyl)noroxymorphone; Nalbuphone

Chemical Property of 6-Keto Nalbuphine

Chemical Property:

• PSA: 70.00000
• LogP: 1.85340

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A metabolite of Nalbuphine (N232500).

Technology Process of 6-Keto Nalbuphine

There total 2 articles about 6-Keto Nalbuphine 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:

cyclobutylaldehyde (2987-17-9) + (-)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride (52446-24-9) → nalbuphine (20594-83-6) + (4R,4aS,7aR,12bS)-3-(cyclobutylmethyl)-4a,9-dihydroxy-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7(7aH)-one (16676-33-8)

Guidance literature:

cyclobutylaldehyde; (-)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride; With acetic acid; tetramethylammonium triacetoxyborohydride; In N,N-dimethyl-formamide; at 20 ℃;

With acetic acid; tetramethylammonium triacetoxyborohydride; In N,N-dimethyl-formamide; at 60 ℃; Solvent;

DOI:10.1021/acs.oprd.0c00321

Reference yield:

noroxymorphone (33522-95-1) → nalbuphine (20594-83-6) + (4R,4aS,7aR,12bS)-3-(cyclobutylmethyl)-4a,9-dihydroxy-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7(7aH)-one (16676-33-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrogenchloride / water; tetrahydrofuran / 20 °C / Inert atmosphere; Reflux; Large scale

2.1: acetic acid; tetramethylammonium triacetoxyborohydride / N,N-dimethyl-formamide / 20 °C

2.2: 60 °C

With hydrogenchloride; acetic acid; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/acs.oprd.0c00321

Reference yield: 97.0%

(4R,4aS,7aR,12bS)-3-(cyclobutylmethyl)-4a,9-dihydroxy-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7(7aH)-one (16676-33-8) → nalbuphine (20594-83-6)

Guidance literature:

With phosphoric acid; hydrogen; 10 % platinum on carbon; In water; isopropyl alcohol; at 50 ℃; for 7h; under 2068.65 Torr; pH=6.49;

upstream raw materials:

cyclobutylaldehyde

(-)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride

noroxymorphone

Downstream raw materials:

nalbuphine

nalbuphine hydrochloride

6β-hydroxy-17-cyclobutylmethyl-4,5α-epoxy-3,14-dihydroxymorphinan

2,2'-bisnalbuphine