Name: 486-70-4|((1R,9aR)-Octahydro-1H-quinolizin-1-yl)methanol|95%
Brand: Ambeed
SKU: A658166
Rating: 90 (22 reviews)

1
[ 122-04-3 ]
[ 486-70-4 ]
[ 38734-34-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine In benzene 1) 0 - 2 deg C, 40 min; 2) 2 --> 20 deg C, 3 h; 3) 70 deg C, 50 min;
	With benzene
	With toluene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]
[2]Kaznel'son; Kabatschnik [Doklady Akademii Nauk SSSR, 1935, p. I 125,127][Chem.Abstr., 1937, p. 3493]
[3]Kaznel'son; Kabatschnik [Doklady Akademii Nauk SSSR, 1935, p. I 125,127][Chem.Abstr., 1937, p. 3493]

2
[ 486-70-4 ]
[ 23506-89-0 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride
	With thionyl chloride
	With thionyl chloride In chloroform Reflux;

With thionyl chloride In benzene

Reference： [1]Orechoff; Menschikoff [Chemische Berichte, 1931, vol. 64, p. 266,273] Karrer; Vogt [Helvetica Chimica Acta, 1930, vol. 13, p. 1075] Sadykow [Zhurnal Obshchei Khimii, 1949, vol. 19, p. 143,146; engl. Ausg. S. 131]
[2]Ercoli, Marcella; Mina, Lorenzo; Boido, Caterina Canu; Boido, Vito; Sparatore, Fabio; Armani, Ugo; Piana, Antonietta [Il Farmaco, 2004, vol. 59, # 2, p. 101 - 109]
[3]Rusconi, Chiara; Vaiana, Nadia; Casagrande, Manolo; Basilico, Nicoletta; Parapini, Silvia; Taramelli, Donatella; Romeo, Sergio; Sparatore, Anna [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5980 - 5985]
[4]Fazylov, S. D.; Makhmutova, A. S.; Nurkenov, O. A.; Nurmaganbetov, Zh. S.; Satpaeva, Zh. B.; Turdybekov, D. M.; Turdybekov, K. M. [Journal of Structural Chemistry, 2020, vol. 61, # 11, p. 1823 - 1826][Zh. Strukt. Kim., 2020, vol. 61, # 11, p. 1920 - 1923,4]

3
[ 486-70-4 ]
[ 486-71-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium; benzene
	Multi-step reaction with 2 steps 1: 2.5 percent / NaH / xylene / 5 h / Heating 2: NaBH₄ / ethanol; H₂O / 3 h / Heating

Reference： [1]Krieg,K. [Diss.<Marburg 1928>,S.29,32] Schoepf et al. [Chemische Berichte, 1931, vol. 64, p. 683,691] Winterfeld; Holschneider [Chemische Berichte, 1931, vol. 64, p. 137,142, 147, 148]
[2]Sparatore, Anna; Tasso, Bruno; Boido, Vito; Sparatore, Fabio [Helvetica Chimica Acta, 2005, vol. 88, # 2, p. 245 - 251]

4
[ 10248-30-3 ]
[ 486-70-4 ]

Yield	Reaction Conditions	Operation in experiment
	With L-Tartaric acid Gewinnung aus dem Racemat;
	Multi-step reaction with 2 steps 1.1: Amano Lipase AK / toluene / 19 h 1.2: 10 h / 20 °C 2.1: sodium hydroxide; water / methanol / 1 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1.1: Amano Lipase PS / toluene / 24 h 1.2: 24 h / 20 °C 2.1: sodium hydroxide; water / methanol / 1 h / 0 - 20 °C

Reference： [1]Clemo; Morgan; Raper [Journal of the Chemical Society, 1938, p. 1574]
[2]Rusconi, Chiara; Vaiana, Nadia; Casagrande, Manolo; Basilico, Nicoletta; Parapini, Silvia; Taramelli, Donatella; Romeo, Sergio; Sparatore, Anna [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5980 - 5985]
[3]Rusconi, Chiara; Vaiana, Nadia; Casagrande, Manolo; Basilico, Nicoletta; Parapini, Silvia; Taramelli, Donatella; Romeo, Sergio; Sparatore, Anna [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5980 - 5985]

5
[ 16100-91-7 ]
[ 486-70-4 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride In diethyl ether at 25℃; for 8h;

Reference： [1]Hua; Miao; Bravo; Takemoto [Synthesis, 1991, # 11, p. 970 - 974]

6
[ 138713-64-1 ]
[ 486-70-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With nickel In ethanol at 25℃; for 10h;

Reference： [1]Hua; Miao; Bravo; Takemoto [Synthesis, 1991, # 11, p. 970 - 974]

7
[ 23164-47-8 ]
[ 486-70-4 ]
Methyl-phosphonic acid butyl ester (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With triethylamine In diethyl ether

Reference： [1]Dalimov, D. N.; Gafurov, M. B.; Vaizburg, G. M.; Abduvakhabov, A. A.; Godovikov, N. N. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1987, vol. 36, # 3, p. 594 - 597][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 3, p. 650 - 654]

8
[ 22103-85-1 ]
[ 486-70-4 ]
2-Benzoyl-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

9
[ 1711-09-7 ]
[ 486-70-4 ]
3-Bromo-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

10
[ 15110-09-5 ]
[ 486-70-4 ]
[ 112653-64-2 ]

Yield	Reaction Conditions	Operation in experiment
46%	With triethylamine In diethyl ether

Reference： [1]Dalimov, D. N.; Gafurov, M. B.; Vaizburg, G. M.; Abduvakhabov, A. A.; Godovikov, N. N. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1987, vol. 36, # 3, p. 594 - 597][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 3, p. 650 - 654]

11
[ 18005-37-3 ]
[ 486-70-4 ]
Methyl-phosphonothioic acid O-[(1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl] ester O-propyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With triethylamine In diethyl ether

Reference： [1]Dalimov, D. N.; Gafurov, M. B.; Vaizburg, G. M.; Abduvakhabov, A. A.; Godovikov, N. N. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1987, vol. 36, # 3, p. 594 - 597][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 3, p. 650 - 654]

12
[ 53864-20-3 ]
[ 486-70-4 ]
Methyl-phosphonic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester pentyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With triethylamine In diethyl ether

Reference： [1]Dalimov, D. N.; Gafurov, M. B.; Vaizburg, G. M.; Abduvakhabov, A. A.; Godovikov, N. N. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1987, vol. 36, # 3, p. 594 - 597][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 3, p. 650 - 654]

13
[ 20540-93-6 ]
[ 486-70-4 ]
Methyl-phosphonothioic acid O-[(1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl] ester O-pentyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With triethylamine In diethyl ether

Reference： [1]Dalimov, D. N.; Gafurov, M. B.; Vaizburg, G. M.; Abduvakhabov, A. A.; Godovikov, N. N. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1987, vol. 36, # 3, p. 594 - 597][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 3, p. 650 - 654]

14
[ 3282-30-2 ]
[ 486-70-4 ]
[ 139293-56-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine In benzene at 60 - 70℃; for 3h;

Reference： [1]Tlegenov, R. T.; Khaitbaev, Kh.; Tilyabaev, E.; Dalimov, D. N.; Abduvakhabov, A. A.; Uteniyazov, K. U. [Chemistry of Natural Compounds, 1991, vol. 27, # 1, p. 55 - 57][Khimiya Prirodnykh Soedinenii, 1991, # 1, p. 64 - 67]

15
[ 102-92-1 ]
[ 486-70-4 ]
[ 139403-39-7 ]

Yield	Reaction Conditions	Operation in experiment
82.3%	With triethylamine In benzene at 20℃; for 4h;	Synthesis of O-Cinnamoyllupinine (1) A solution of lupinine (3 g, 17.75 mmol) in C6H6 (50 mL) was stirred,treated with Et3N (2.47 mL, 17.75 mmol) and a solution of 3-phenylacrylic acid chloride (2.95 g, 17.75 mmol) in C6H6(20 mL), and stirred for 4 h at room temperature as a precipitate formed. The precipitate of Et3NHCl was filtered off. Thefiltrate was evaporated. The residue was chromatographed over Al2O3 (petroleum ether-C6H6 eluent) to afford 1 (2.47 g,82.3%) as yellow crystals with mp 77-78°C. The elemental analysis agreed with that calculated for C19H25NO2. 1 NMRspectrum (400 MHz, DMSO-d6, δ, ppm, J/Hz): 1.09-1.15 (1, m, -8), 1.31-1.35 (5, m, -3, 4, 7, 9), 1.43-1.46(1H, m, -9eq), 1.52-1.55 (1H, m, -3eq), 1.61-1.64 (1, m, H-8eq), 1.74-1.89 (5, m, H-4eq, 5, 6, 2ax, 10ax), 2.66-2.69(2, m, H-2eq, 10eq), 4.22-4.35 (2, m, -11), 6.58 (1, d, J = 16.0, -13), 7.60 (1, d, J = 18.3, -14), 7.37-7.38 (3, m,-16, 18, 20), 7.66 (2, br.s, -17, 19). 13C NMR spectrum (100 MHz, DMSO-d6, δ, ppm): 21.12 (-3), 25.14 (-8), 25.74(-9), 27.23 (-4), 29.81 (-7), 37.81 (-5), 57.42 (-2, 10), 63.57 (-11), 64.34 (-6), 118.67 (-13), 128.88 (-17, 19),129.43 (-16, 20), 130.96 (-18), 134.54 (-15), 144.92 (-14), 166.80 (-12). HMQC NMR spectrum (1H-13C): 4ax-4(1.30, 27.26), 4eq-4 (1.78, 27.20), 3ax-3 (1.20, 27.26), 3eq-3 (1.52, 27.26), 7-7 (1.40, 29.65), 5-5 (1.87, 37.78),2ax,10ax-2,10 (1.77, 57.13), 2eq,10eq-2,10 (2.66, 57.17), 13-13 (6.60, 118.64), 18-18 (7.36, 130.98), 16-16 (7.37,129.42), 17-17 (7.67, 128.92) and 14-14 (7.62, 144.93).
47%	With triethylamine In benzene at 60 - 70℃;

Reference： [1]Nurkenov; Nurmaganbetov, Zh. S.; Fazylov; Satpaeva, Zh. B.; Turdybekov; Seilkhanov; Talipov [Chemistry of Natural Compounds, 2019, vol. 55, # 3, p. 506 - 508][Khim. Prir. Soedin., 2019, vol. 55, # 3, p. 434 - 436,3]
[2]Tlegenov, R. T.; Khaitbaev, Kh.; Tilyabaev, E.; Dalimov, D. N.; Abduvakhabov, A. A.; Uteniyazov, K. U. [Chemistry of Natural Compounds, 1991, vol. 27, # 1, p. 55 - 57][Khimiya Prirodnykh Soedinenii, 1991, # 1, p. 64 - 67]

16
[ 618-46-2 ]
[ 486-70-4 ]
3-Chloro-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

17
[ 609-65-4 ]
[ 486-70-4 ]
2-Chloro-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

18
[ 2524-16-5 ]
[ 486-70-4 ]
O-ethyl-O-lupinanyl methylthiophosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With triethylamine In diethyl ether

Reference： [1]Dalimov, D. N.; Gafurov, M. B.; Vaizburg, G. M.; Abduvakhabov, A. A.; Godovikov, N. N. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1987, vol. 36, # 3, p. 594 - 597][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 3, p. 650 - 654]

19
[ 874-60-2 ]
[ 486-70-4 ]
4-Methyl-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

20
[ 122-01-0 ]
[ 486-70-4 ]
4-Chloro-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

21
[ 100-07-2 ]
[ 486-70-4 ]
4-Methoxy-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

22
[ 27611-63-8 ]
[ 486-70-4 ]
2-Cyano-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

23
[ 7154-66-7 ]
[ 486-70-4 ]
2-Bromo-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

24
[ 1711-11-1 ]
[ 486-70-4 ]
3-Cyano-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

25
[ 21615-34-9 ]
[ 486-70-4 ]
2-Methoxy-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

26
[ 18005-38-4 ]
[ 486-70-4 ]
Methyl-phosphonothioic acid O-butyl ester O-[(1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl] ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With triethylamine In diethyl ether

Reference： [1]Dalimov, D. N.; Gafurov, M. B.; Vaizburg, G. M.; Abduvakhabov, A. A.; Godovikov, N. N. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1987, vol. 36, # 3, p. 594 - 597][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 3, p. 650 - 654]

27
[ 586-75-4 ]
[ 486-70-4 ]
4-Bromo-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

28
[ 108-12-3 ]
[ 486-70-4 ]
[ 129133-61-5 ]

Yield	Reaction Conditions	Operation in experiment
79%	With triethylamine In benzene at 60 - 70℃;

Reference： [1]Tlegenov, R. T.; Khaitbaev, Kh.; Tilyabaev, E.; Dalimov, D. N.; Abduvakhabov, A. A.; Uteniyazov, K. U. [Chemistry of Natural Compounds, 1991, vol. 27, # 1, p. 55 - 57][Khimiya Prirodnykh Soedinenii, 1991, # 1, p. 64 - 67]

29
[ 76-02-8 ]
[ 486-70-4 ]
[ 139293-57-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine In benzene at 60 - 70℃;

Reference： [1]Tlegenov, R. T.; Khaitbaev, Kh.; Tilyabaev, E.; Dalimov, D. N.; Abduvakhabov, A. A.; Uteniyazov, K. U. [Chemistry of Natural Compounds, 1991, vol. 27, # 1, p. 55 - 57][Khimiya Prirodnykh Soedinenii, 1991, # 1, p. 64 - 67]

30
[ 121-90-4 ]
[ 486-70-4 ]
3-Nitro-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

31
[ 610-14-0 ]
[ 486-70-4 ]
2-Nitro-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

32
[ 486-70-4 ]
[ 1711-06-4 ]
3-Methyl-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

33
[ 486-70-4 ]
[ 1441-87-8 ]
2-Hydroxy-benzoic acid (1R,9aR)-1-(octahydro-quinolizin-1-yl)methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With triethylamine In benzene

Reference： [1]Sadykov, A. S.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Ishbaev, A. A.; Gafurova, Sh. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1983, vol. 32, # 11, p. 2338 - 2344][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 11, p. 2599 - 2606]

34
[ 1476-39-7 ]
[ 90-39-1 ]
[ 486-70-4 ]

Reference： [1]Journal of Chemical Research, Miniprint,1987,p. 2101 - 2120

35
[ 213884-66-3 ]
[ 486-70-4 ]

Yield	Reaction Conditions	Operation in experiment
66%	With lithium aluminium tetrahydride; hydrogen In tetrahydrofuran for 12h;

Reference： [1]Mangeney, Pierre; Hamon, Louis; Raussou, Sabine; Urbain, Nicolas; Alexakis, Alexandre [Tetrahedron, 1998, vol. 54, # 35, p. 10349 - 10362]

36
[ 5176-08-9 ]
[ 486-70-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With copper(II) sulfate In dimethyl sulfoxide

Reference： [1]Ledoux, Stéphane; Marchalant, Elisabeth; Célérier, Jean-Pierre; Lhommet, Gérard [Tetrahedron Letters, 2001, vol. 42, # 32, p. 5397 - 5399]

37
[ 725250-71-5 ]
[ 486-70-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: (1R)-(9aR)-octahydro-quinolizine-1-carboxylic acid methyl ester With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 3h; Inert atmosphere; Reflux; Stage #2: With Glauber's salt In tetrahydrofuran; diethyl ether	4.11. Synthesis of [(9R,9aR)-octahydro-1H-quinolizin-9-yl]methanol [(-)-lupinine, 2] A solution of quinolizidine ester 12 (78 mg, 0.396 mmol) in THF (1 mL) was added dropwise to a suspension of lithium aluminum hydride (21 mg, 0.60 mmol) in Et2O (7 mL). The resulting mixture was refluxed for 3 h, then cooled and Na2SO4·10H2O was added under vigorous stirring until aluminum salts turned white. The suspension was filtered through a short pad of Celite washing with small portions of diethyl ether. The filtrate was concentrated under vacuum and the residue was purified by flash chromatography (CH2Cl2/MeOH/NH4OH, 97:3:0.1 to 95:5:0.1) to give (-)-lupinine 2 as a white solid (60 mg, 90% yield). Mp 66-68 °C [lit.refPreviewPlaceHolder14 mp 70-71 °C]. -20.1 (c 1.0, EtOH) [lit.refPreviewPlaceHolder14 -21.0 (c 0.25, EtOH)]. The spectroscopic data are in agreement with those previously reported in the literature.refPreviewPlaceHolder141H NMR (300 MHz, CDCl3) δ 1.15-1.30 (m, 1H), 1.52-1.58 (m, 6H), 1.74-1.80 (m, 4H), 1.99-2.14 (m, 3H), 2.77-2.81 (m, 2H), 3.67 (d, J=10.8 Hz, 1H), 4.09-4.14 (m, 1H), 4.75 (br s, 1H). 13C NMR (75.5 MHz, CDCl3) δ 22.8 (CH2), 24.5 (CH2), 25.5 (CH2), 29.5 (CH2), 31.2 (CH2), 38.1 (CH), 57.0 (2CH2), 65.0 (CH), 65.7 (CH2). HRMS (EI+) calcd for C10H20NO [M++H] 170.1545, found 170.1542.
60%	With lithium aluminium tetrahydride In tetrahydrofuran for 15h; Heating;

Reference： [1]Location in patent: experimental part Fustero, Santos; Moscardó, Javier; Sánchez-Roselló, María; Flores, Sonia; Guerola, Marta; Pozo, Carlos Del [Tetrahedron, 2011, vol. 67, # 38, p. 7412 - 7417]
[2]Agami, Claude; Dechoux, Luc; Hebbe, Séverine; Ménard, Cécilia [Tetrahedron, 2004, vol. 60, # 25, p. 5433 - 5438]

38
[ 108-05-4 ]
[ 486-70-4 ]
(1R,9aR)-1-(vinyloxymethyl)octahydroquinolizine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With sulfuric acid; mercury(II) diacetate at 60℃; for 27h;

Reference： [1]Oparina; Tlegenov; Ermakova; Kuznetsova; Kanitskaya; Tantsyrev; Trofimov [Russian Chemical Bulletin, 2004, vol. 53, # 1, p. 242 - 244]

39
[ 486-70-4 ]
[ 74-86-2 ]
(1R,9aR)-1-(vinyloxymethyl)octahydroquinolizine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 105 - 110℃; for 3h;

Reference： [1]Oparina; Tlegenov; Ermakova; Kuznetsova; Kanitskaya; Tantsyrev; Trofimov [Russian Chemical Bulletin, 2004, vol. 53, # 1, p. 242 - 244]

40
[ 486-70-4 ]
[ 486-71-5 ]
[ 851183-14-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 57% 2: 2.5%	With sodium hydride In xylene for 5h; Heating;

Reference： [1]Sparatore, Anna; Tasso, Bruno; Boido, Vito; Sparatore, Fabio [Helvetica Chimica Acta, 2005, vol. 88, # 2, p. 245 - 251]

41
[ 753452-08-3 ]
[ 7635-60-1 ]
[ 486-70-4 ]