1001338-53-9

Basic information

• Product Name: (4R,9aR)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2one
• Synonyms: (4R,9aR)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2one
• CAS NO: 1001338-53-9
• Molecular Weight: 289.375
• Mol File: 1001338-53-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (4R,9aR)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2one(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,9aR)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2one(1001338-53-9)
• EPA Substance Registry System: (4R,9aR)-4-(3,4-dimethoxyphenyl)octahydro-2H-quinolizin-2one(1001338-53-9)

Safety Data

• Hazardous Substances Data: 1001338-53-9(Hazardous Substances Data)

Upstream product

• 80245-51-8 4-lithio-1,2-dimethoxybenzene 
• 144409-59-6 (R)-7,8,9,9a-tetrahydro-1H-quinolizin-2(6H)-one 
• 126378-42-5 4-methoxy-3-(trisopropylsilyl)pyridine 
• 144375-66-6 4-Methoxy-1-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyloxycarbonyl]-3-triisopropylsilanyl-pyridinium; chloride 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 110-89-4 piperidine 
• 2156-71-0 N-chloropiperidine 
• 522-33-8 Tripiperidin 
• 15001-27-1 O-methyldehydrozingerone 
• 184535-17-9 (-)-(2S)-(2-oxopropyl)piperidine-1-carbamic acid benzyl ester 
• 184535-06-6 (+)-(2R)-(2-oxopropyl)piperidine-1-carbamic acid benzyl ester 
• 2508-29-4 5-hydroxypentylamine 
• 2858-67-5 1-[(2S)-piperidin-2-yl]acetone 
• 2858-66-4 (-)-pelletierine 

Downstream Products

• 913626-91-2 (2S,4R,9aR)-4-(3,4-dimethoxyphenyl)octahydro-1H-quinolizin-2-ol 

Relevant articles and documents

Catalytic enantioselective approach to the stereodivergent synthesis of (+)-lasubines I and II

(Chemical Equation Presented) A concise and efficient approach to the stereodivergent synthesis of (+)-lasubines I and II is described. The key common intermediate is a chiral N-sulfonyl 2,3-dihydropyridone obtained by a novel Cu-catalyzed asymmetric form

Strategies for the Asymmetric Construction of Pelletierine and its Use in the Synthesis of Sedridine, Myrtine, and Lasubine

Three methods for the asymmetric synthesis of both enantiomers of pelletierine 6 are reported. Bella's proline-based Mannich process gave (R)- and (S)-Cbz-protected 6 in good yields from Δ1-piperideine 14 and in reasonable enantiomeric excess (74–80 % ee). An intramolecular aza-Michael, cinchona-based, organocatalytic method is also reported. With commercially available 9-amino quinine (24a) and quinidine (24b) catalysts, Cbz-protected α,β-unsaturated ketone 23 also gave (R)- and (S)-Cbz-protected 6 in good yields and enantiomeric excess (90–99 % ee). This material was used to synthesize both optically active forms of deoxyhalofuginone (26), an analogue of febrifugine which is of interest as an anti-fibrotic agent. Finally, a resolution of racemic pelletierine using (R)- and (S)-mandelic acid 27 is reported. This scalable method gave both enantiomers of Cbz- and Boc-protected 6 in excellent enantiomeric excess (≥ 99 %). Both highly enantioenriched forms of 6 (obtained from the resolution study) were used to synthesize several alkaloids. Firstly, (–)-(S)-Cbz-protected pelletierine 17 was used to prepare naturally occurring sedridine (32) and its epimer allosedridine (8). Then the preparation of both enantiomers of the quinolizidine myrtine (33) by an olefination-intramolecular aza-Michael sequence is reported. Finally, the synthesis of the epimeric quinolizidine alkaloids, lasubine I (34) and lasubine II (35), from (+)- and (–)-Boc-protected pelletierine (29) respectively, is discussed.

Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates. Asymmetric syntheses of the quinolizidine alkaloids (+)-myrtine, (-)-lasubine I, and (+)-subcosine I

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