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Name Phenylephrine hydrochloride;SLV-325;Incostop;Neo-Synephrine hydrochloride;Nostril;Mydfrin;Biomydrin;Alcon Efrin
Chemical Name (-)-3-[1(R)-Hydroxy-2-(methylamino)ethyl]phenol hydrochloride
CAS 61-76-7
Related CAS 59-42-7 (free base)
Formula C9H14ClNO2
Structure
Formula Weight 203.67043
Stage 上市
Company Solvay (Marketer), SLA Pharma (Licensee)
Activity/Mechanism Anorectal Disorders, Treatment of, GASTROINTESTINAL DRUGS
Syn. Route 1
Route 1
3-hydroxybenzaldehyde (i) was protected as the methoxyethoxymethyl ether derivative (ii) by treatment with methoxyethoxymethyl chloride and diisopropyl ethyl amine. subsequent condensation of (ii) with dimethyloxosulfonium methylide, generated from oxosulfonium salt (iii) and nah, gave rise to the racemic epoxide (iv). kinetic resolution by hydrolysis with (r,r)-n,n-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt (iii) acetate complex provided the (s)-diol (v) along with the unreacted (r)-epoxide (vi), which were separated by column chromatography. opening of the desired (r)-epoxide (vi) with methanolic methylamine gave amino alcohol (vii). finally, removal of the methoxyethoxymethyl group by refluxing in methanolic hcl furnished the title compound.
List of intermediates No.
benzhydryl (7r)-7-amino-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
5,8-dimethyl-2h-chromene-3-carbaldehyde (i)
benzhydryl (2r)-3-[(acetoxy)methyl]-8-oxo-7-[(z)-2-pyridinylmethylidene]-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate (iii)
(4s,7r,8s,9s)-4-[[tert-butyl(dimethyl)silyl]oxy]-8-hydroxy-5,5,7,9-tetramethyl-12-((2r,3s)-2-methyl-3-[(2s,3e)-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-2-[(triethylsilyl)oxy]-3-butenyl]oxiranyl)-1-dodecen-6-one (ii)
(1s,2r,5s)-5-[[tert-butyl(dimethyl)silyl]oxy]-2,4,4-trimethyl-1-[(1s)-1-methyl-4-((2r,3s)-2-methyl-3-[(2s,3e)-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-2-[(triethylsilyl)oxy]-3-butenyl]oxiranyl)butyl]-3-oxo-7-octenyl 2,2,2-trichloroethyl carbonate (iv)
(3s,6r,7s,8s)-3-[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8-tetramethyl-11-((2r,3s)-2-methyl-3-[(2s,3e)-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-2-[(triethylsilyl)oxy]-3-butenyl]oxiranyl)-5-oxo-7-[[(2,2,2-trichloroethoxy)carbonyl]oxy]undecanoic acid (v)
(3s,6r,7s,8s)-3-[[tert-butyl(dimethyl)silyl]oxy]-11-[(2r,3s)-3-[(2s,3e)-2-hydroxy-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)-3-butenyl]-2-methyloxiranyl]-4,4,6,8-tetramethyl-5-oxo-7-[[(2,2,2-trichloroethoxy)carbonyl]oxy]undecanoic acid (vi)
(1s,3s,7s,10r,11s,12s,16r)-7-[[tert-butyl(dimethyl)silyl]oxy]-8,8,10,12,16-pentamethyl-3-[(e)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)ethenyl]-5,9-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-11-yl 2,2,2-trichloroethyl carbonate (vii)
2-(hydroxyamino)-2-methylpropane; n-(tert-butyl)hydroxylamine
Reference 1:
    gurjar, m.k.; et al.; a practical synthesis of (r)-(-)-phenylephrine hydrochloride. org process res dev 1998, 2, 6, 422.

 
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