10248-30-3

Basic information

• Product Name: (1R,9aR)-octahydro-2H-quinolizin-1-ylmethanol(SALTDATA: FREE)
• Synonyms: (1R,9aR)-octahydro-2H-quinolizin-1-ylmethanol(SALTDATA: FREE);((1R)-octahydro-1H-quinolizin-1-yl)methanol;(1R)-octahydro-2H-quinolizin-1-ylmethanol;[(1R)-2,3,4,6,7,8,9,9a-octahydro-1H-quinolizin-1-yl]methanol;[(1R)-quinolizidin-1-yl]methanol
• CAS NO: 10248-30-3
• Molecular Formula: C₁₀H₁₉NO
• Molecular Weight: 169.26396
• Mol File: 10248-30-3.mol
• Article Data: 23

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,9aR)-octahydro-2H-quinolizin-1-ylmethanol(SALTDATA: FREE)(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,9aR)-octahydro-2H-quinolizin-1-ylmethanol(SALTDATA: FREE)(10248-30-3)
• EPA Substance Registry System: (1R,9aR)-octahydro-2H-quinolizin-1-ylmethanol(SALTDATA: FREE)(10248-30-3)

Safety Data

• Hazardous Substances Data: 10248-30-3(Hazardous Substances Data)

Usage

Uses

(±)-Lupinine is used to the synthesis of calcium-channel antagonists.

Purification Methods

It crystallises from Me2CO, pentane and pet ether (b. 40-60o) and can be sublimed or distilled in high vacuum. The picrate has m 127o(from Et2O), the picrolonate has m 203-204o, and the methiodide has m 203o(dec, from EtOH). [Clemo et al. J Chem Soc 969 1937, Boekelheide & Lodge J Am Chem Soc 73 3684 1951, Beilstein 21 II 28, 21 III/IV 291.]

Upstream product

• 127-09-3 sodium acetate 
• 5176-08-9 (+/-)-1t-bromomethyl-(9ar)-octahydro-quinolizin 
• 858261-80-0 5-phenoxy-2-[2]piperidyl-pentan-1-ol 
• 10297-06-0 1-chloro-5-hexyne 
• 90675-48-2 7-Chlor-heptin-⁽²⁾-saeure-ethylester 
• 90642-54-9 ethyl 7-iodo-2-heptynoate 
• 52500-26-2 7-hydroxy-hept-2-ynoic acid methyl ester 
• 135284-85-4 7-oxo-hept-2-ynoic acid methyl ester 
• 147808-88-6 6-methoxycarbonylhex-5-ynoic acid 
• 408330-49-4 1-methyleneoctahydro-1H-quinolizine 
• 120001-35-6 ((4-bromopent-4-en-1-yl)oxy)(tert-butyl)dimethylsilane 
• 694-54-2 tetrahydro-2H-2-pyranol 
• 111022-84-5 (chloro-3-propyl)-1 α-(hexahydropyridylidene)-2 malonate d'isopropylidene 
• 113200-96-7 (chloro-3-propyl)-1 α-(hexahydropyridylidene-2) acetate d'ethyle 

Downstream Products

• 486-70-4 lupinine 
• 10248-22-3 (+/-)-N-Lupinyl-phthalimid 
• 2121-03-1 d,l-chlorolupinane 
• 10248-22-3 2-[(1S,9aR)-octahydro-2H-quinolizin-1-ylmethyl]-1H-isoindol-1,3(2H)-dione 

Relevant articles and documents

Syntheses of Isoretronecanol and Lupinine

Syntheses of (+/-)-isoretronecanol and (+/-)-lupinine are described which employ the 1,3-dipolar additions of cyclic nitrones to dihydrofuran and dihydropyran.The reaction proceeded regio- and stereoselectively to afford the adducts, which were converted into the title compounds by two-step processes.

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An efficient total synthesis of (±)-epilupinine and (±)-lupinine from a common quinolizidine intermediate

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β-ENAMINOESTERS BICYCLIQUES : SYNTHESE ET REDUCTION STEREOSPECEFIQUES. ACCES A L'ISORETRONECANOL, LA TRACHELANTHAMIDINE, LA LUPININE ET L'EPILUPININE

The functionalized N-alkyl-β-enaminoesters 11 are precursore of nitrogen-bridged bicyclic β-enaminoesters 7.The compounds 7 are prepared either by intramolecular alkylation of β-enaminoesters 11 or by termolysis of β-enaminoesters 6.A stereospecific reduction of 7 under thermal control leads to bicyclic β-aminoesters 13, 14, 15 or 16 which are good precursors of natural aminoalcohols like lupinine 4 or isoretronecanol 2.

Synthesis of Substituted Quinolizidines via a Gold-Catalyzed Double Cyclization Cascade

A novel synthesis of quinolizidines by a cationic gold-catalyzed double cyclization cascade has been developed. The reaction was initiated by the gold-catalyzed 6-exo-dig cyclization of ynamides, which was followed by a second cyclization of an enamide intermediate to provide the corresponding quinolizidine derivatives. The utility of this reaction was demonstrated by application to the synthesis of multi-substituted quinolizidines and by the total synthesis of a quinolizidine alkaloid, (±)-lupinine.

Synthesis and comparison of antiplasmodial activity of (+), (-) and racemic 7-chloro-4-(N-lupinyl)aminoquinoline

Recently the N-(-)-lupinyl-derivative of 7-chloro-4-aminoquinoline ((-)-AM-1; 7-chloro-4-{N-[(1S,9aR)(octahydro-2H-quinolizin-1-yl)methyl]amino} quinoline) showed potent in vitro and in vivo activity against both Chloroquine susceptible and resistant strains of Plasmodium falciparum. However, (-)-AM-1 is synthesized starting from (-)-lupinine, an expensive alkaloid isolated from Lupinus luteus whose worldwide production is not sufficient, at present, for large market purposes. To overcome this issue, the corresponding racemic compound, derived from synthetic (±)-lupinine was considered a cheaper alternative for the development of a novel antimalarial agent. Therefore, the racemic and the 7-chloro-4-(N-(+)-lupinyl)aminoquinoline ((±)-AM-1; (+)-AM-1) were synthesized and their in vitro antimalarial activity and cytotoxicity compared with those of (-)-AM-1. The (+)-lupinine required for the synthesis of (+)-AM-1 was obtained through a not previously described lipase catalyzed kinetic resolution of (±)-lupinine. In terms of antimalarial activity, (±)-AM1 and (+)-AM1 demonstrated very good activity in vitro against both CQ-R and CQ-S strains of P. falciparum (range IC50 16-35 nM), and low toxicity against human normal cell lines (therapeutic index >1000), comparable with that of (-)-AM1. These results confirm that the racemate (±)-AM1 could be considered as a potential antimalarial agent, ensuring a decrease of costs of synthesis compared to (-)-AM1.