6beta-Nalbuphine

Base Information

• Chemical Name: 6beta-Nalbuphine
• CAS No.: 85284-04-4
• Molecular Formula: C₂₁H₂₇NO₄
• Molecular Weight: 357.45
• DSSTox Substance ID: DTXSID601337963
• Nikkaji Number: J1.014.449C
• Mol file: 85284-04-4.mol

Synonyms:6beta-Nalbuphine;DTXSID601337963;85284-04-4

Chemical Property of 6beta-Nalbuphine

Chemical Property:

• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 357.19400834
• Heavy Atom Count: 26
• Complexity: 597

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(C1)CN2CCC34C5C(CCC3(C2CC6=C4C(=C(C=C6)O)O5)O)O
• Isomeric SMILES: C1CC(C1)CN2CC[C@]34[C@@H]5[C@@H](CC[C@]3([C@H]2CC6=C4C(=C(C=C6)O)O5)O)O

Technology Process of 6beta-Nalbuphine

There total 5 articles about 6beta-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:

(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) → 6β-hydroxy-17-cyclobutylmethyl-4,5α-epoxy-3,14-dihydroxymorphinan (85284-04-4) + nalbuphine (20594-83-6)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 25 ℃; for 1h;

Reference yield:

noroxymorphone (33522-95-1) → 6β-hydroxy-17-cyclobutylmethyl-4,5α-epoxy-3,14-dihydroxymorphinan (85284-04-4) + nalbuphine (20594-83-6)

Guidance literature:

Multi-step reaction with 3 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

3.1: sodium tetrahydroborate / dimethyl sulfoxide / 60 °C

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

DOI:10.1021/acs.oprd.0c00321

Reference yield:

(-)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride (52446-24-9) → 6β-hydroxy-17-cyclobutylmethyl-4,5α-epoxy-3,14-dihydroxymorphinan (85284-04-4) + nalbuphine (20594-83-6)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 60 °C

2.1: sodium tetrahydroborate / dimethyl sulfoxide / 60 °C

With sodium tetrahydroborate; acetic acid; tetramethylammonium triacetoxyborohydride; In dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/acs.oprd.0c00321

upstream raw materials:

(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

noroxymorphone

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