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52446-24-9

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Basic Information
CAS No.: 52446-24-9
Name: (5alpha)-4,5-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride
Article Data: 6
Molecular Structure:
Molecular Structure of 52446-24-9 ((5alpha)-4,5-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride)
Formula: C16H17 N O4 . Cl H
Molecular Weight: 323.776
Synonyms: Morphinan-6-one,4,5-epoxy-3,14-dihydroxy-, hydrochloride, (5a)- (9CI); 7,8-Dihydro-14-hydroxynormorphinonehydrochloride; Noroxymorphone hydrochloride
Density: g/cm3
Boiling Point: 566.9°Cat760mmHg
Flash Point: 296.7°C
PSA: 78.79000
LogP: 1.53380
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(-)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride

Conditions
ConditionsYield
With Wilkinson's catalyst In 1,4-dioxane; water at 150℃; for 1h; Microwave irradiation; Inert atmosphere;99%
With Wilkinson's catalyst In water at 200℃; for 1.5h; Microwave irradiation;
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noroxymorphone

52446-24-9

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

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water at 20℃; Inert atmosphere; Reflux; Large scale;93.2%
With hydrogenchloride In water at 90℃;
52446-24-9

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

6-α-noroxymorphinol hydrochloride

Conditions
ConditionsYield
With acetic acid; tetramethylammonium triacetoxyborohydride In dimethyl sulfoxide at 50℃; for 5h;99.5%
52446-24-9

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

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cyclopropylcarbinyl bromide

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Naltrexone

Conditions
ConditionsYield
Stage #1: (-)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride With sodium hydrogencarbonate In ISOPROPYLAMIDE at 65 - 69℃; for 0.166667h;
Stage #2: cyclopropylcarbinyl bromide In ISOPROPYLAMIDE at 69℃; for 6.5h;
Stage #3: With sodium hydroxide; water In ISOPROPYLAMIDE pH=8.6 - 9;		88.6%
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3-maleimidopropionic acid N-hydroxysuccinimide ester

52446-24-9

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

C23H22N2O7

Conditions
ConditionsYield
Stage #1: (-)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: 3-maleimidopropionic acid N-hydroxysuccinimide ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 1.5h; Inert atmosphere;		82%
2987-17-9

cyclobutylaldehyde

52446-24-9

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

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nalbuphine

Conditions
ConditionsYield
Stage #1: cyclobutylaldehyde; (-)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride With acetic acid; tetramethylammonium triacetoxyborohydride In dimethyl sulfoxide at 20℃; for 1h; Large scale;
Stage #2: With acetic acid; tetramethylammonium triacetoxyborohydride In dimethyl sulfoxide at 60℃; Solvent; Reagent/catalyst; Large scale;		77.7%
2987-17-9

cyclobutylaldehyde

52446-24-9

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

16676-34-9

6-ketonalbuphine hydrochloride

Conditions
ConditionsYield
Stage #1: cyclobutylaldehyde; (-)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride In dimethyl sulfoxide at 20℃; for 0.5h;
Stage #2: With acetic acid; tetramethylammonium triacetoxyborohydride In dimethyl sulfoxide at 20℃; for 1.16667h;
Stage #3: With hydrogenchloride In water; isopropyl alcohol Solvent; Reagent/catalyst;		67.6%
52446-24-9

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

6-β-noroxymorphinol hydrochloride

Conditions
ConditionsYield
Stage #1: (-)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride With sodium hydroxide In water
Stage #2: With Aminoiminomethanesulfinic acid; sodium hydroxide In water at 85℃; for 1h; Inert atmosphere;
Stage #3: With hydrogenchloride In water at 20℃; for 3.5h;		44%
52446-24-9

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

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bromoacetylglycyne N-hydroxysuccinimide ester

C20H21BrN2O6

Conditions
ConditionsYield
Stage #1: (-)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Inert atmosphere;
Stage #2: bromoacetylglycyne N-hydroxysuccinimide ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 1.33333h; Inert atmosphere;		19.3%
42014-51-7

bromoacetic acid N-hydroxusuccinimidyl ester

52446-24-9

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

noroxymorphone bromoacetamide

Conditions
ConditionsYield
Stage #1: (-)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.0833333h;
Stage #2: bromoacetic acid N-hydroxusuccinimidyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;
Stage #3: With sodium bromide In acetone at 56℃; for 24h; Inert atmosphere;
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