[ CAS No. 75208-40-1 ] {[proInfo.proName]}

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Quality Control of [ 75208-40-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 75208-40-1 ]

SDS Specification

Alternatived Products of [ 75208-40-1 ]

Product Details of [ 75208-40-1 ]

CAS No. :	75208-40-1	MDL No. :	MFCD06797960
Formula :	C₈H₁₃NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	155.19	Pubchem ID :	-
Synonyms :

Safety of [ 75208-40-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 75208-40-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 75208-40-1 ]

[ 75208-40-1 ] Synthesis Path-Downstream 1~23

1
[ 51627-76-0 ]
[ 75208-40-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride for 3h; Heating;

Reference： [1]Orlek, Barry S.; Blaney, Frank E.; Brown, Frank; Clark, Michael S. G.; Hadley, Michael S.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2726 - 2735]

2
[ 67-56-1 ]
[ 75208-40-1 ]
[ 38206-86-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride for 12h; Heating; Yield given;

Reference： [1]Orlek, Barry S.; Blaney, Frank E.; Brown, Frank; Clark, Michael S. G.; Hadley, Michael S.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2726 - 2735]

3
[ 6238-33-1 ]
[ 75208-40-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With water for 3h; Heating;
	With hydrogenchloride for 5h; Heating;
	With hydrogenchloride Heating;

Reference： [1]Koikov, L. N.; Lisitsa, E. A.; Alekseeva, N. A.; Turchin, K. F.; Filipenko, T. Ya. [Chemistry of Heterocyclic Compounds, 1992, vol. 28, # 11, p. 1289 - 1292][Khimiya Geterotsiklicheskikh Soedinenii, 1992, # 11, p. 1509 - 1512]
[2]Bromidge, Steven M.; Brown, Frank; Cassidy, Frederick; Clark, Michael S. G.; Dabbs, Steven; Hadley, Michael S.; Hawkins, Julie; Loudon, Julia M.; Naylor, Christopher B.; Orlek, Barry S.; Riley, Graham J. [Journal of Medicinal Chemistry, 1997, vol. 40, # 26, p. 4265 - 4280]
[3]Tatsumi, Ryo; Seio, Kohji; Fujio, Masakazu; Katayama, Jiro; Horikawa, Takashi; Hashimoto, Kenji; Tanaka, Hiroshi [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3781 - 3784]

4
[ 75208-40-1 ]
[ 142643-14-9 ]
C₃₁H₄₅N₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane for 18h;

Reference： [1]Nargund, Ravi P.; Barakat, Khaled H.; Cheng, Kang; Chan, Wanda W.-S; Butler, Bridget R.; Smith, Roy G.; Patchett, Arthur A. [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 11, p. 1265 - 1270]

5
[ 75208-40-1 ]
[ 83598-29-2 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride In dichloromethane for 4h; Heating;
	With thionyl chloride

Reference： [1]Bromidge, Steven M.; Brown, Frank; Cassidy, Frederick; Clark, Michael S. G.; Dabbs, Steven; Hadley, Michael S.; Hawkins, Julie; Loudon, Julia M.; Naylor, Christopher B.; Orlek, Barry S.; Riley, Graham J. [Journal of Medicinal Chemistry, 1997, vol. 40, # 26, p. 4265 - 4280]
[2]Tatsumi, Ryo; Seio, Kohji; Fujio, Masakazu; Katayama, Jiro; Horikawa, Takashi; Hashimoto, Kenji; Tanaka, Hiroshi [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3781 - 3784]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride

7
[ 75208-40-1 ]
[ 133366-37-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ 2: Et₃N

Reference： [1]Tatsumi, Ryo; Seio, Kohji; Fujio, Masakazu; Katayama, Jiro; Horikawa, Takashi; Hashimoto, Kenji; Tanaka, Hiroshi [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 14, p. 3781 - 3784]

8
[ 75208-40-1 ]
3-benzo[<i>b</i>]thiophen-2-ylmethyl-1-aza-bicyclo[2.2.2]octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: SOCl₂ 2: Et₃N 3: 42 percent / -78 °C 4: NaBH₄ 5: NaI; TMSCl / acetonitrile

9
[ 75208-40-1 ]
(1-aza-bicyclo[2.2.2]oct-3-yl)-benzo[<i>b</i>]thiophen-2-yl-methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: SOCl₂ 2: Et₃N 3: 42 percent / -78 °C 4: NaBH₄

10
[ 75208-40-1 ]
[ 392287-48-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: SOCl₂ 2: Et₃N 3: 42 percent / -78 °C

11
[ 75208-40-1 ]
[ 149156-47-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ / CH₂Cl₂ / 4 h / Heating 2: 92 percent / pyridine / acetonitrile; CHCl₃ / 2 h / Ambient temperature

12
[ 75208-40-1 ]
[ 155613-14-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: SOCl₂ / CH₂Cl₂ / 4 h / Heating 2: 92 percent / pyridine / acetonitrile; CHCl₃ / 2 h / Ambient temperature 3: 57 percent / CCl₄, Ph₃P / acetonitrile / 0.33 h / Heating

13
[ 75208-40-1 ]
[R,S]-α-(methoxyimino)-α-(1-azabicyclo[2.2.2]oct-3-yl)acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: SOCl₂ / CH₂Cl₂ / 4 h / Heating 2: 92 percent / pyridine / acetonitrile; CHCl₃ / 2 h / Ambient temperature 3: 57 percent / CCl₄, Ph₃P / acetonitrile / 0.33 h / Heating 4: dimethylsulfoxide / 7 h / 95 °C

14
[ 75208-40-1 ]
[ 151433-82-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: SOCl₂ / CH₂Cl₂ / 4 h / Heating 2: 92 percent / pyridine / acetonitrile; CHCl₃ / 2 h / Ambient temperature 3: 57 percent / CCl₄, Ph₃P / acetonitrile / 0.33 h / Heating 4: dimethylsulfoxide / 7 h / 95 °C

15
[ 75208-40-1 ]
sabcomeline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: SOCl₂ / CH₂Cl₂ / 4 h / Heating 2: 92 percent / pyridine / acetonitrile; CHCl₃ / 2 h / Ambient temperature 3: 57 percent / CCl₄, Ph₃P / acetonitrile / 0.33 h / Heating 4: dimethylsulfoxide / 7 h / 95 °C

16
[ 75208-40-1 ]
(S)-1-Aza-bicyclo[2.2.2]oct-3-yl-[(Z)-methoxyimino]-acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: SOCl₂ / CH₂Cl₂ / 4 h / Heating 2: 92 percent / pyridine / acetonitrile; CHCl₃ / 2 h / Ambient temperature 3: 57 percent / CCl₄, Ph₃P / acetonitrile / 0.33 h / Heating 4: dimethylsulfoxide / 7 h / 95 °C

17
[ 75208-40-1 ]
(Z)-N-methoxy-1-azabicyclo[2.2.2]octane-3-carboximidoyl fluoride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: SOCl₂ / CH₂Cl₂ / 4 h / Heating 2: 92 percent / pyridine / acetonitrile; CHCl₃ / 2 h / Ambient temperature 3: 57 percent / CCl₄, Ph₃P / acetonitrile / 0.33 h / Heating 4: CsF/CaF₂ / dimethylformamide / 120 h / 145 °C

18
[ 3731-38-2 ]
[ 75208-40-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 74 percent / t-BuOK, EtOH / 1,2-dimethoxy-ethane / 1.) 5-10 deg C, 0.5 h, 2.) 40 deg C, 2.5 h 2: concd HCl / 3 h / Heating

Reference： [1]Orlek, Barry S.; Blaney, Frank E.; Brown, Frank; Clark, Michael S. G.; Hadley, Michael S.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2726 - 2735]

19
[ 75208-40-1 ]
[ 114725-06-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: HCl / 12 h / Heating 2: 0.36 g / N₂H₄*H₂O / 2 h / 120 °C

Reference： [1]Orlek, Barry S.; Blaney, Frank E.; Brown, Frank; Clark, Michael S. G.; Hadley, Michael S.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2726 - 2735]

20
[ 75208-40-1 ]
[ 114724-71-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: HCl / 12 h / Heating 2: 0.36 g / N₂H₄*H₂O / 2 h / 120 °C 3: 72 percent / 4 h / 120 - 140 °C

Reference： [1]Orlek, Barry S.; Blaney, Frank E.; Brown, Frank; Clark, Michael S. G.; Hadley, Michael S.; et al. [Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2726 - 2735]

21
[ 75208-40-1 ]
[ 66073-50-5 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride In toluene for 2h; Heating / reflux;	1A 3-Quinuclidinecarbonyl chloride hydrochloride EXAMPLE 1A 3-Quinuclidinecarbonyl chloride Hydrochloride 3-Quinuclidinecarboxylic acid hydrochloride was prepared as described by Orlek et al. J. Med. Chem. 1991, 34, 2726. 500 mg (2.61 mmol) of 3-quinuclidinecarboxylic acid are heated together with 1.9 ml (26.09 mmol) of thionyl choride under reflux for 2 h. The reaction mixture is freed of excess thionyl chloride under reduced pressure. 20 ml portions of toluene are added twice and evaporated to dryness each time. The product obtained in this way is reacted immediately without further purification.

Reference： [1]Current Patent Assignee: BAYER AG - US2005/107460, 2005, A1 Location in patent: Page/Page column 6

22
[ 75208-40-1 ]
[ 138874-55-2 ]
[(3S)-quinuclidin-3-yl]methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / diethyl ether; tetrahydrofuran / 73 h / 20 °C / Inert atmosphere; Cooling with ice 2: Supercritical conditions; Resolution of racemate
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 73 h / 20 °C / Inert atmosphere; Cooling with ice 2: Resolution of racemate; Supercritical conditions

Reference： [1]Current Patent Assignee: Valline SRL - WO2016/193240, 2016, A1
[2]Current Patent Assignee: Valline SRL - WO2016/193244, 2016, A1

23
[ 75208-40-1 ]
[ 5176-22-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 20℃; for 73h; Inert atmosphere; Cooling with ice;	A solution of quinuclidine-3-carboxylic acid (665 mg, 4.28 mmol) in dry THF (7 mL) was stirred under N2 and cooled in an ice-water bath. A 2 M solution of LiA1H4 in Et20 (4.3 mL, 8.56 mmol) was added dropwise over a period of 10 minutes. The mixture was stirred in an ice bath for one hour then allowed to warm to room temperature and stirred for 72 hours. The mixture was cooled in an ice-bath and a 1 N solution of NaOH (1 mL) was added dropwise over a period of 10 minutes followed by water (0.5 mL). The mixture was stirred at room temperature for one hour and then filtered through a Celite cartridge which was then washed through with a small amount of THF and water. The combinedfiltrates were concentrated in vacuo to give a racemic mixture of the title product as a colourless oil. (792 mg, 76%).LCMS (Method 2): [MH+] = 142 at 0.60 mm.
76%	With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 20℃; for 73h; Inert atmosphere; Cooling with ice;	Intermediate 3 and Intermediate 4 [(3S)-quinuclidin-3-yl] methanol (1-3) and [(3R)-quinuclidinyl] methanol (1-4) A solution of (665 mg, 4.28 mmol) in dry THF (7 mL) was stirred under N2 and cooled in an ice-water bath. A 2 M solution of LiAlH4 in Et20 (4.3 mL, 8.56 mmol) was added dropwise over a period of 10 minutes. The mixture was stirred in an ice bath for one hour then allowed to warm to room temperature and stirred for 72 hours. The mixture was cooled in an ice-bath and a 1 N aqueous solution of NaOH (1 mL) was added dropwise over a period of 10 minutes followed by water (0.5 mL). The mixture was stirred at room temperature for one hour, and then filtered through a Celite cartridge which was then washed through with a small amount of THF and water. The combined filtrates were concentrated in vacuo to give a racemic mixture of the title product as a colourless oil (792 mg, 76%). LCMS (Method 2): [MH+] = 142 at 0.60 min.Purification of the mixture of enantiomers by chiral preparative SFC afforded the single enantiomers Title compound (Intermediate 3, single enantiomer 1) was obtained as a light brown gum (235 mg, 59%). LCMS (Method 4): [MH+] = 142 at 0.62 min. Chiral analysis (Method 5) at 9.56 min. [a] = -51.17 0 (c = 0.3 g/100 mL, CH3OH).Title compound (Intermediate 4, single enantiomer 2) was obtained as a light brown gum (203 mg, 51%). LCMS (Method 4): [MH+] = 142 at 0.61 min. Chiral analysis (Method 5) at 1 1.28 min. [a]2D° = +36.33 0 (c = 0.3 g/100 mL, CH3OH).

Reference： [1]Current Patent Assignee: Valline SRL - WO2016/193244, 2016, A1 Location in patent: Page/Page column 64; 65
[2]Current Patent Assignee: Valline SRL - WO2016/193240, 2016, A1 Location in patent: Page/Page column 39; 40

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[ CAS No. 75208-40-1 ] {[proInfo.proName]}

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Product Details of [ 75208-40-1 ]

Safety of [ 75208-40-1 ]

Application In Synthesis of [ 75208-40-1 ]

[ 75208-40-1 ] Synthesis Path-Downstream 1~23

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Health hazards

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