CAS No.509-66-0,3-methoxy-17-methyl-8,14-didehydro-4,5-epoxymorphinan-6-one Suppliers

Products Categories

Pharmaceutical (20)
Others (4)
Organic Chemicals (1)

Basic Information

Molecular Structure:
CAS No.:	509-66-0
Name:	3-methoxy-17-methyl-8,14-didehydro-4,5-epoxymorphinan-6-one
Article Data:	12

Formula:	C₁₈H₁₉NO₃
Molecular Weight:	297.354
Synonyms:	Nicodicodinum [INN-Latin];Nicodicodina [DCIT];Nicodicodinum;Nicodicodine [INN:BAN:DCF];Nicodicodine;Dihydrocodein-nicotinat (ester);6-Nicotinoyl dihydrocodeine;Nicodicodina;
Density:	1.34g/cm³
Boiling Point:	470°Cat760mmHg
Flash Point:	238°C
PSA:	38.77000
LogP:	1.79130

Synthetic route

: 5140-31-8
(+)-14β-bromocodeinone

: 509-66-0
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol; chloroform under 760 Torr; for 5h; Ambient temperature;

: 32398-20-2
neopinone dimethyl acetal

: 509-66-0
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one

Conditions

Conditions	Yield
With hydrogenchloride

: 115-37-7
thebaine

: 509-66-0
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one

Conditions

Conditions	Yield

Multi-step reaction with 3 steps 1: N-bromo-acetamide 2: H2, aq. NaOH / Pd-C / methanol 3: aq. HCl View Scheme
Multi-step reaction with 2 steps 1: NBS / acetone; H2O 2: H2 / Pd-C / CHCl3; methanol / 5 h / 760 Torr / Ambient temperature View Scheme

: 28406-17-9
14-bromo-4,5α-epoxy-3-methoxy-17-methyl-(14ξ)-morphin-7-en-6-one; hydrochloride

: 509-66-0
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one

Conditions

Conditions	Yield
With sodium sulfite

: 102422-72-0
3a(R),9b(S)-dihydro-5-methoxy-9b-<2-(N-methylammonio)ethyl>phenanthro<4,4a,4b,5-bcd>furan-3(8H)-one trifluoroacetate

A: 509-66-0
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one

B: C18H19NO3

C: 467-13-0
codeinone

Conditions

Conditions	Yield
With sodium hydrogencarbonate In chloroform; water for 0.333333h; Yield given. Yields of byproduct given;

...Expand

14-bromo-codeinone: 14-bromo-codeinone

: 509-66-0
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one

Conditions

Conditions	Yield
With methanol; palladium on activated charcoal; chloroform

: 1422-07-7
codeine hydrochloride

A: 509-66-0
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one

B: 467-13-0
codeinone

Conditions

Conditions	Yield
With alcohol dehydrogenase from Thermoanaerobium brockii; β-nicotinamide dinucleotide phosphate sodium salt; morphine dehydrogenase from Pseudomonas putida M10 In phosphate buffer at 30℃; for 24h; Title compound not separated from byproducts.;

: 76-57-3
codeine

A: 509-66-0
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one

B: 467-13-0
codeinone

Conditions

Conditions	Yield
With β-nicotinamide dinucleotide phosphate sodium salt; NADP+-dependent morphine dehydrogenase; 1-(3-hydroxypropyl)-3-methylimidazolium glycolate; water In phosphate buffer at 30℃; for 24h; Title compound not separated from byproducts.;

: 4599-09-1
14-bromo-4,5α-epoxy-3,6,6-trimethoxy-17-methyl-(14ξ)-morphin-7-ene

: 509-66-0
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2, aq. NaOH / Pd-C / methanol 2: aq. HCl View Scheme

: 916225-97-3
2-iodo-6-methoxy-3-(2,2-dimethoxyethyl)phenol

: 509-66-0
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0.5 h / 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); triethylamine; tris-(o-tolyl)phosphine / acetonitrile / 1 h / 85 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 70 °C 3.2: 0.17 h / 20 °C 4.1: camphor-10-sulfonic acid / methanol / 6 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C 6.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C 7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 8.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 8.2: 0.5 h / 20 °C View Scheme
Multi-step reaction with 7 steps 1.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine / acetonitrile / 2 h / 85 °C 3.1: camphor-10-sulfonic acid / methanol / 6 h / 20 °C 4.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C 5.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 7.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 7.2: 0.5 h / 20 °C View Scheme

Yield

Multi-step reaction with 8 steps
1.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0.5 h / 20 °C
2.1: tris-(dibenzylideneacetone)dipalladium(0); triethylamine; tris-(o-tolyl)phosphine / acetonitrile / 1 h / 85 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 70 °C
3.2: 0.17 h / 20 °C
4.1: camphor-10-sulfonic acid / methanol / 6 h / 20 °C
5.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C
6.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C
8.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C
8.2: 0.5 h / 20 °C
View Scheme

Multi-step reaction with 7 steps
1.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 20 °C
2.1: tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine / acetonitrile / 2 h / 85 °C
3.1: camphor-10-sulfonic acid / methanol / 6 h / 20 °C
4.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C
5.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C
7.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C
7.2: 0.5 h / 20 °C
View Scheme