Production Method 1

24424-99-5

56-41-7

100-52-7

321-97-1

90-81-3

Reaction Conditions

1.1R:NaOH, S:Dioxane, S:H2O, 0°C, pH 9; overnight, rt
2.1R:NaOH, S:THF, cooled; 24 h, rt
2.2S:H2O, rt
3.1R:F3CCO2H, S:CH2Cl2, rt; 24 h, rt
4.1S:DMSO, 1 h, 130°C
4.2R:AcOH, 4 h, reflux

Reference

Profiling ephedrine prepared from N-methylalanine via the Akabori-Momotani reaction

By Doddridge, Alexandra et al, Drug Testing and Analysis, 2018, 10(3), 548-556

Production Method 2

18107-18-1

181646-92-4

52305-20-1

321-97-1

1262432-94-9

Reaction Conditions

1.1R:LiN(Pr-i)2, S:THF, -78°C
1.2R:LiCl, -78°C
1.3S:THF, -78°C; 1 h, -78°C; -78°C → rt; 30 min, rt; rt → -100°C
1.4S:THF, 20 min, -100°C; 7 h, -100°C
1.5R:NH4Cl, S:H2O, -100°C; -100°C → rt
2.1S:H2O, S:MeOH, S:Dioxane
2.2R:NaOH, rt → reflux; 2 h, reflux; reflux → rt
2.3S:H2O, rt
2.4R:HCl, S:H2O, rt, pH 3
2.5S:THF, rt → 0°C
2.62 h, 0°C
2.7S:MeOH, 45 min
2.8S:H2O

Reference

Role of Pseudoephedrine as Chiral Auxiliary in the "Acetate-Type" Aldol Reaction with Chiral Aldehydes; Asymmetric Synthesis of Highly Functionalized Chiral Building Blocks

By Ocejo, Marta et al, Journal of Organic Chemistry, 2011, 76(2), 460-470

Production Method 3

1798-60-3

321-97-1

Reaction Conditions

1.1R:NaBH4, S:EtOH

Reference

Reductive aminations of carbonyl compounds with borohydride and borane reducing agents

By Baxter, Ellen W. and Reitz, Allen B., Organic Reactions (Hoboken, 2002, 59, No pp. given

Production Method 4

321-97-1

321-97-1

Reaction Conditions

1.1R:KH, S:THF, 18 h, rt
1.224 h, rt
1.3R:Me2CHOH

Reference

Evaluation of a Pseudoephedrine Linker for Asymmetric Alkylations on Solid Phase

By Hutchison, Panee C. et al, Organic Letters, 2002, 4(26), 4583-4585

Production Method 5

2216-51-5

94100-69-3

100-52-7

321-97-1

Reaction Conditions

1.1R:HCl, R:MgSO4, S:CH2Cl2
2.1R:EtN(Pr-i)2, S:CH2Cl2
3.1
4.1R:O3, S:MeOH, S:CH2Cl2
4.2R:Me2S
4.3R:AgNO3, S:H2O
4.4R:NaOH, S:H2O
5.1R:Et3N, R:(PhO)2P(=O)N3, S:Benzene
6.1R:LiAlH4, S:THF

Reference

Synthesis of optically active (E)-1-alkoxymethoxybut-2-enyl(tributyl)stannanes: stereochemistry of their thermal reactions with aldehydes

By Jephcote, Vincent J. et al, Journal of the Chemical Society, 1989, (8), 1529-35

Production Method 6

1798-60-3

321-97-1

Reaction Conditions

1.1S:Et2O
1.2R:Zn(BH4)2, S:Et2O

Reference

Stereoselective syntheses of ephedrine and related 2-amino alcohols of high optical purity from protected cyanohydrins

By Jackson, W. Roy et al, Tetrahedron Letters, 1990, 31(10), 1447-50

Production Method 7

100-52-7

101986-32-7

321-97-1

Reaction Conditions

1.1R:LiN(Pr-i)2, S:THF, S:(Me2N)3P=O
1.2
2.1R:LiN(Pr-i)2, S:THF, S:(Me2N)3P=O
2.2
2.3R:NaBH4, S:EtOH
3.1R:H2, C:Pd hydroxide, S:MeOH

Reference

A new and simple synthesis of (+)- and (-)-threo-ephedrine

By Marco, Jose L., Journal of Chemical Research, 1988, (2), 51

Production Method 8

321-97-1

Reaction Conditions

1.1C:283594-89-8, S:H2O, pH 8

Reference

Directed evolution of an aminoalcohol dehydrogenase for efficient production of double chiral aminoalcohols

By Urano, Nobuyuki et al, Journal of Bioscience and Bioengineering, 2011, 111(3), 266-271

Production Method 9

4125-58-0

321-97-1

Reaction Conditions

1.1

Reference

Synergistic effects on enantioselectivity of zwitterionic chiral stationary phases for separations of chiral acids, bases, and amino acids by HPLC

By Hoffmann, Christian V. et al, Analytical Chemistry (Washington, 2008, 80(22), 8780-8789

Production Method 10

55116-41-1

321-97-1

Reaction Conditions

1.1R:t-BuOK, R:H2, C:930607-62-8, S:Me2CHOH, 9 h, 30°C, 8 atm
2.1R:NaOH, S:H2O, S:EtOH, 12 h, reflux

Reference

Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by the TolBINAP/DMAPEN-Ruthenium(II) Complex: A Significant Effect of N-Substituents of Chiral 1,2-Diamine Ligands on Enantioselectivity

By Ooka, Hirohito et al, Journal of Organic Chemistry, 2008, 73(22), 9084-9093

Production Method 11

24424-99-5

18162-48-6

4407-36-7

321-97-1

Reaction Conditions

1.1R:t-BuOOH, R:(+)-Di-i-Pr tartrate, C:Ti(OPr-i)4, S:CH2Cl2
2.1S:H2O, S:MeOH
3.1R:1H-Imidazole, S:CH2Cl2
4.1R:PPh3, R:N2(CO2CHMe2)2, S:Et2O
4.2R:NaI, S:Me2CO
5.1R:KF, S:MeOH
6.1S:C5H5N
6.2R:HCl, S:H2O
7.1R:NaBH4, S:DMSO
8.1R:KOH, S:H2O, S:EtOH
8.2R:NH4Cl, S:H2O

Reference

Asymmetric synthesis of (-)-pseudoephedrine from (2S,3S)-3-phenyloxiran-2-ylmethanol. Stereospecific interchange of amino and alcohol functions

By Testa, M. L. et al, Tetrahedron: Asymmetry, 2001, 12(9), 1369-1372

(-)-Pseudoephedrine Raw materials

• L(-)-Menthol
• (-)-Pseudoephedrine
• Di-tert-butyl dicarbonate
• tert-butyl(chloro)dimethylsilane
• Benzamide, N-methyl-N-(1-methyl-2-oxo-2-phenylethyl)-
• (E)-Cinnamyl Alcohol
• 2-Buten-1-ol, 1-(tributylstannyl)-, (E)-
• L-Alanine
• (diazomethyl)trimethylsilane
• (+) ephedrine
• Benzaldehyde
• (R)-1-Hydroxy-1-phenylpropanone
• 3-Oxazolidineacetonitrile, 4-phenyl-, (R)-
• Carbamic acid, [(1R)-1-formyl-2-phenylethyl]methyl-, 1,1-dimethylethyl ester (9CI)
• ACETAMIDE, N-[(1R,2R)-2-HYDROXY-1-METHYL-2-PHENYLETHYL]-N-METHYL-

(-)-Pseudoephedrine Preparation Products

• (-)-Pseudoephedrine (321-97-1)
• D-erythro-Pentonic acid, 2,4,5-trideoxy-4-[[(1,1-dimethylethoxy)carbonyl]methylamino]-5-phenyl-, methyl ester (1262432-94-9)
• Benzenemethanol, a-[(1R)-1-(methylamino)ethyl]-, (aS)-rel- (90-81-3)

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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Phenylpropanes

• 50906-05-3(Ephedrine hemihydrate)
• 42151-56-4(Benzenemethanol, a-[(1R)-1-(dimethylamino)ethyl]-,(aS)-)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)