140-55-6

Basic information

• Product Name: pseudoconhydrine
• Synonyms: (3R)-trans-6-propylpiperidin-3-ol; (3S,6S)-6-propylpiperidin-3-ol; 6-propylpiperidin-3-ol
• CAS NO: 140-55-6
• Molecular Formula: C₈H₁₇NO
• Molecular Weight: 143.2267
• Mol File: 140-55-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 106°; mp 60° from moist ether
• Boiling Point: 236°C at 760 mmHg
• Flash Point: 90.7°C
• Density: 0.932g/cm³
• Vapor Pressure: 0.00879mmHg at 25°C
• Refractive Index: 1.458
• PKA: pK (18°): 3.70
• CAS DataBase Reference: pseudoconhydrine(CAS DataBase Reference)
• NIST Chemistry Reference: pseudoconhydrine(140-55-6)
• EPA Substance Registry System: pseudoconhydrine(140-55-6)

Safety Data

• Hazardous Substances Data: 140-55-6(Hazardous Substances Data)

Upstream product

• 1242338-31-3 (2R,5S)-1-benzyloxycarbonyl-5-(tert-butyldimethylsilyloxy)-2-(propa-1,2-dienyl)piperidine 
• 92599-71-8 methyl 2-propylpiperidine-1-carboxylate 
• 1451214-40-6 (1’R,3S,6S)-1-(2’-hydroxy-1’-phenylethyl)-6-propylpiperidin-3-ol 
• 1451214-39-3 (3R,6S)-3-phenylhexahydrooxazolo[3,2-a]pyridin-6-yl acetate 
• 1451214-37-1 (1S,1’R)-1-[(2’-benzyloxy-1’-phenylethylamino)methyl]-3-[1,3]dioxolan-2-ylpropyl acetate 
• 1451214-33-7 (1’R,2S)-1-(2’-benzyloxy-1’-phenylethyl)-2-(2-[1,3]dioxolan-2-ylethyl)aziridine 
• 179748-56-2 (+/-)-N-Carbobenzoxy-3-hydroxy-1,2,3,4-tetrahydropyridine 
• 109-00-2 3-HYDROXYPYRIDINE 
• 503560-92-7 (6S,1'R)-(-)-N-(1-phenylbutoxy)-6-non-1-enylamine 
• 185758-26-3 (S)-2-Propyl-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 168418-67-5 (S)-N-(benzyloxycarbonyl)-1-propyl-5-hexenylamine 
• 272788-19-9 N-[5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-propyl-pentyl]-4-methyl-benzenesulfonamide 
• 272788-18-8 N-[5-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-propyl-pent-2-enyl]-4-methyl-benzenesulfonamide 

Downstream Products

• 155511-85-6 (2S,5S)-(+)-1-(benzyloxycarbonyl)-5-hydroxy-2-propylpyperidine 

Relevant articles and documents

Novel reduction of 3-hydroxypyridine and its use in the enantioselective synthesis of (+)-pseudoconhydrine and (+)-N-methylpseudoconhydrine

3-Hydroxypyridine is reduced with sodium borohydride in the presence of benzyl chloroformate to give 1-benzyloxycarbonyl-5-hydroxy-2-piperideine which is transformed into (+)-pseudoconhydrine and (+)-N-methylpseudoconhydrine in five steps involving a lipa

Enantioselective Preparation and Hydroboration of Cyclic Enamides: Synthesis of (2S)-Pseudoconhydrine

Successive treatment of 2-alkyl-1-hydroxy-6-carbonylsultampiperidines 1 with NaH and an acylating agent/pyridine in boiling toluene affords optically pure 1-acyl-2-alkyl-1,2,3,4-tetrahydropyridines 2.Hydroboration/oxidation of N-benzoylenamides 2f and 2g furnishes trans-2-alkyl-1-benzyl-5-hydroxypiperidines 5f and 5g, respecively.Hydrogenolysis of 5f provides pure (2S)-pseudoconhydrine (7), in 3 steps from 1, R2=n-C3H7 (31percent overall yield).

A novel route to 6-substituted piperidin-3-ols via domino cyclization of 2-hydroxy-6-phosphinyl-5-hexenyl tosylates with primary amines: Synthesis of (±)-pseudoconhydrine and (±)- epi -pseudoconhydrine

2-Hydroxy-6-phosphinyl-5-hexenyl tosylates, oxirane ring-opening products derived from glycidyl tosylates and phosphinyl-substituted allyl anions, undergo domino SN2-Michael reactions with primary amines to give 6-phosphinylmethylpiperidin-3-ols. The phosphinyl unit can be used in Horner olefination reactions. This approach is applied to the synthesis of racemic pseudoconhydrine and its epimer. Georg Thieme Verlag Stuttgart New York.

Asymmetric syntheses of pyrrolidine and piperidine derivatives Via regio-and stereo-selective ring-opening reactions of chiral aziridine

Asymmetric synthesis of cyclic β-amino alcohols (pyrrolidine and piperidine derivatives) has been achieved using a chiral aziridine as the starting material. The key step of this synthetic methodology is regio- and stereo-controlled ring-opening of the chiral aziridine with acetic acid or acetyl chloride.