159345-06-9

Basic information

• Product Name: (1S,2S)-PSEUDOEPHEDRINE-(R)-2-METHYLHYDR
• Synonyms: (1S,2S)-PSEUDOEPHEDRINE-(R)-2-METHYLHYDR
• CAS NO: 159345-06-9
• Molecular Formula: C₂₀H₂₅NO₂
• Molecular Weight: 311.422
• Product Categories: Asymmetric Synthesis;Chiral Auxiliaries;Ephedrine Derivatives
• Mol File: 159345-06-9.mol

Chemical Properties

• Melting Point: 136-140 °C(lit.)
• Boiling Point: 483.4°C at 760 mmHg
• Flash Point: 246.2°C
• Appearance: /
• Density: 1.091g/cm³
• Vapor Pressure: 3.71E-10mmHg at 25°C
• Refractive Index: 1.567
• PKA: 13.70±0.20(Predicted)
• CAS DataBase Reference: (1S,2S)-PSEUDOEPHEDRINE-(R)-2-METHYLHYDR(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-PSEUDOEPHEDRINE-(R)-2-METHYLHYDR(159345-06-9)
• EPA Substance Registry System: (1S,2S)-PSEUDOEPHEDRINE-(R)-2-METHYLHYDR(159345-06-9)

Safety Data

• Hazardous Substances Data: 159345-06-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1S,2S)-PSEUDOEPHEDRINE-(R)-2-METHYLHYDR is used as a decongestant for its sympathomimetic effects, which help to relieve nasal congestion by constricting blood vessels in the nasal passages.
Used in Regulatory Purposes:
(1S,2S)-PSEUDOEPHEDRINE-(R)-2-METHYLHYDR is regulated and restricted in many countries due to its potential for misuse in the illegal production of methamphetamine.

InChI:InChI=1/C20H25NO2/c1-15(14-17-10-6-4-7-11-17)20(23)21(3)16(2)19(22)18-12-8-5-9-13-18/h4-13,15-16,19,22H,14H2,1-3H3/t15-,16+,19-/m1/s1

Upstream product

• 108-90-7 chlorobenzene 
• 90-82-4 pseudoephedrine 
• 100-39-0 benzyl bromide 
• 159213-03-3 N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide 

Downstream Products

• 192060-54-1 (2S,4S,6S)-2,4,6-Trimethyl-7-phenyl-heptanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 192060-53-0 (2S,4R,6S)-2,4,6-Trimethyl-7-phenyl-heptanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 191927-42-1 (2R,4S,6S)-2,4,6-Trimethyl-7-phenyl-heptanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 191927-40-9 (2R,4R,6S)-2,4,6-Trimethyl-7-phenyl-heptanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 
• 191927-38-5 ((2S,4R)-5-Iodo-2,4-dimethyl-pentyl)-benzene 
• 192574-01-9 (1R,2S,7R,8R)-2-Benzyloxy-1-[(S)-2-((1S,2R)-3-benzyloxy-1-benzyloxymethyl-1,2-dihydroxy-propyl)-oxiranyl]-7-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-8-methyl-9-phenyl-nonan-3-one 
• 192574-00-8 (2R,3S,5S,6S,11R,12R)-1,6-Bis-benzyloxy-3-benzyloxymethyl-11-(tert-butyl-dimethyl-silanyloxy)-2,3,5-trihydroxy-12-methyl-4-methylene-13-phenyl-tridecan-7-one 
• 192573-95-8 (1S,3R,4S,5R,6R,7S)-7-Benzyloxy-3,4-bis-benzyloxymethyl-1-[(4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-5-hydroxymethyl-2,8-dioxa-bicyclo[3.2.1]octane-4,6-diol 
• 192573-98-1 (1R,4R,5R,6S)-6-Benzyloxy-4-((E)-3-benzyloxy-1-benzyloxymethyl-propenyl)-1-[(4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-6-phenyl-hexyl]-2,7-dioxa-bicyclo[2.2.1]heptan-5-ol 
• 192573-93-6 [(R)-4-Benzenesulfonyl-1-((R)-1-methyl-2-phenyl-ethyl)-butoxy]-tert-butyl-dimethyl-silane 
• 192573-92-5 (2R,3R)-6-Benzenesulfonyl-2-methyl-1-phenyl-hexan-3-ol 
• 154920-05-5 (2R,3R)-2-methyl-1-phenyl-hex-5-en-3-ol 

Relevant articles and documents

Palladium-catalyzed suzuki-miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides

Figure Presented. Enantiomerically enriched potassium β- trifluoroboratoamides were synthesized as air-stable solids in greater than 95:5 dr using pseudoephedrine as the chiral auxiliary. With these chiral nucleophiles, Suzuki-Miyaura cross-coupling react

Syntheses of the C-1 alkyl side chains of Zaragozic acids A and C

Asymmetric syntheses of the C-1 alkyl side chains of Zaragozic acids A and C from a common chiral precursor 4 are reported. The stereoselective reduction of unsaturated ketones 8 and 10 is the key step of both syntheses.

Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones

The use of pseudoephedrine as a practical chiral auxiliary for asymmetric synthesis is described in full. Both enantiomers of pseudoephedrine are inexpensive commodity chemicals and can be N-acylated in high yields to form tertiary amides. In the presence of lithium chloride, the enolates of the corresponding pseudoephedrine amides undergo highly diastereoselective alkylations with a wide range of alkyl halides to afford α-substituted products in high yields. These products can then be transformed in a single operation into highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones.

Asymmetric synthesis of 1,3-dialkyl-substituted carbon chains of any stereochemical configuration by an iterable process

A highly practical, iterable method for the preparation of 1,3,5,n(odd)-polyalkyl-substituted carbon chains based upon the asymmetric alkylation of pseudoephedrine amide enolates is described.

Studies towards the synthesis of the zaragozic acids: Synthesis of the bicyclic acetal core of zaragozic acid C.

The bicyclic core 6 of zaragozic acid C (7) was prepared by the epoxide cyclisation reaction 21 → 22 → 15. Acetal 15 was also obtained by acid-promoted rearrangement of the isomeric acetal 19.