[ CAS No. 67571-90-8 ] {[proInfo.proName]}

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Quality Control of [ 67571-90-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 67571-90-8 ]

CAS No. :	67571-90-8	MDL No. :	MFCD11045502
Formula :	C₁₃H₁₈N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	202.30	Pubchem ID :	-
Synonyms :

Safety of [ 67571-90-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 67571-90-8 ]

* 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.

Upstream synthesis route of [ 67571-90-8 ]
Downstream synthetic route of [ 67571-90-8 ]

[ 67571-90-8 ] Synthesis Path-Upstream 1~4

1
[ 67571-90-8 ]
[ 149771-44-8 ]

Reference： [1] Tetrahedron Letters, 2002, vol. 43, # 5, p. 899 - 902
[2] Farmaco, 1998, vol. 53, # 8-9, p. 557 - 562
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 5, p. 674 - 681
[4] Farmaco, 1993, vol. 48, # 3, p. 387 - 396
[5] Patent: US9404081, 2016, B2,

2
[ 24424-99-5 ]
[ 67571-90-8 ]
[ 149771-44-8 ]

Reference： [1] Patent: WO2006/106090, 2006, A1,

3
[ 24424-99-5 ]
[ 67571-90-8 ]
[ 149771-43-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With triethylamine In dichloromethane at 0℃; for 3 h;	3-Benzyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (Intermediate); A mixture of 3-benzyl-3,8-diaza-bicyclo[3.2.1]octane (13.5 g, 66.7 mmol), triethylamine (6.75 g, 66.7 mmol), di-tert-butyl-dicarbonate (boc-anyhdride) (14.56 g, 66.7 mmol) and dichloromethane (100 ml) was stirred with ice-cooling for 3 h. The crude mixture was washed with water (150 ml). The water phase was extracted with dichloromethane (50 ml). The combined organic phase was dried and evaporated. Yield 13 g (65percent). Mp 58-60°C.

Reference： [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 5, p. 674 - 681
[2] Farmaco, 1993, vol. 48, # 3, p. 387 - 396
[3] Patent: EP1213289, 2002, A1, . Location in patent: Page 12
[4] Patent: WO2006/106090, 2006, A1, . Location in patent: Page/Page column 16
[5] Farmaco, 1998, vol. 53, # 8-9, p. 557 - 562
[6] Tetrahedron Letters, 2002, vol. 43, # 5, p. 899 - 902
[7] Patent: US2004/23971, 2004, A1,
[8] Patent: US9404081, 2016, B2, . Location in patent: Page/Page column 178-179

4
[ 24424-99-5 ]
[ 144-55-8 ]
[ 67571-90-8 ]
[ 149771-43-7 ]

Reference： [1] Patent: US2002/128271, 2002, A1,

[ 67571-90-8 ] Synthesis Path-Downstream 1~4

1
[ 501-53-1 ]
[ 149771-44-8 ]
[ 415979-31-6 ]
[ 67571-90-8 ]

Yield	Reaction Conditions	Operation in experiment
		3,8-diazabicyclo[3.2.1]octane-3-carboxylic acid, phenylmethyl ester and 3-(phenylmethyl)-3,8-diazabicyclo[3.2.1]octane. Triethylamine (1.44 mL, 10.363 mmol) was added to a solution of 8-boc-3,8-diaza-bicyclo[3.2.1]ocatane (2.0 g, 9.421 mmol) in CH2Cl2 (20 mL), Benzyl chloroformate (1.46 mL, 10.363 mmol) was added dropwise at 0 C. and the reaction mixture was stirred at 0 C. for 0.5 hr, then allowed to warm to rt. and stirring was continued for 3 days. The reaction mixture was then quenched with water and acidified with 1N HCl solution. The organic layer was separated, washed with brine, dried (MgSO4) and concentrated to give a colorless thick oil as the crude product. 70 mg of this material was then dissolved in 1,2-dichloroethane (2 mL) and TFA (0.5 mL) was added. The reaction mixture was stirred at rt. for 2 hr. The solvent and TFA were then evaporated to give a mixture of the two title compounds as a colorless thick oil.
		Intermediates 29 and 30; <n="70"/>3,8-diazabicyclo[3.2.1]octane-3-carboxylic acid, phenylmethyl ester and 3- (phenylmethyl)-3,8-diazabicyclo [3.2.1] octane. Triethylamine (1.44 mL, 10.363 mmol) was added to a solution of 8-boc-3,8-diaza-bicyclo[3.2. l]ocatane (2.0 g, 9.421 mmol) in CH2CI2 (20 mL), Benzyl chloroformate (1.46 mL, 10.363 mmol) was added dropwise at 00C and the reaction mixture was stirred at 00C for 0.5 hr, then allowed to warm to rt. and stirring was continued for 3 days. The reaction mixture was then quenched with water and acidified with IN HCl solution. The organic layer was separated, washed with brine, dried (MgSO4) and concentrated to give a colorless thick oil as the crude product. 70 mg of this material was then dissolved in 1,2- dichloroethane (2mL) and TFA (0.5 mL) was added. The reaction mixture was stirred at rt. for 2 hr. The solvent and TFA were then evaporated to give a mixture of the two title compounds as a colorless thick oil.

Reference： [1]Patent: US2007/270405,2007,A1 .Location in patent: Page/Page column 50
[2]Patent: WO2009/67108,2009,A1 .Location in patent: Page/Page column 68-69

2
[ 54221-37-3 ]
[ 67571-90-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: toluene / 85 °C 2: xylene / Heating 3: 230 °C 4: H₂; HCl / Pd/C / H₂O / 85 h / 760 Torr 5: LiAlH₄ / diethyl ether / Heating
	Multi-step reaction with 5 steps 1: toluene / 16 h / 85 °C 2: 5,5-dimethyl-1,3-cyclohexadiene / 18 h / Inert atmosphere; Reflux 3: 3 h / 210 - 220 °C / 760.05 Torr 4: hydrogenchloride; palladium 10% on activated carbon; hydrogen / methanol; water / 4 h / 20 °C 5: lithium aluminium tetrahydride / diethyl ether / 30 h / 0 - 20 °C / Inert atmosphere

Reference： [1]Smith, Stephen C; Bentley, Philip D [Tetrahedron Letters, 2002, vol. 43, # 5, p. 899 - 902]
[2]Current Patent Assignee: AGIOS PHARMACEUTICALS INC - US9404081, 2016, B2

3
[ 67571-90-8 ]
[ 149771-44-8 ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 899 - 902
[2]Il Farmaco,1998,vol. 53,p. 557 - 562
[3]Journal of Medicinal Chemistry,1998,vol. 41,p. 674 - 681
[4]Il Farmaco,1993,vol. 48,p. 387 - 396
[5]Patent: US9404081,2016,B2

4
[ 80149-80-0 ]
[ 67571-90-8 ]
[ 845626-29-1 ]

Yield	Reaction Conditions	Operation in experiment
42%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃; for 17.5h;	2-(Trimethylsilyl)ethyl p-nitrophenyl carbonate (1.35 g, 4.78 mmol) in acetonitrile (10 mL) was added to a stirred solution of compound 104 (Tet. Lett. 2002, 899-902, 920 mg, 4.55 mmol), and diisopropylethylamine (0.833 mL, 4.78 mmol) in acetonitrile (10 mL). The reaction was stirred at ambient temperature for 17.5 hours. The solvent was removed in vacuo and the resulting residue was dissolved in ethyl acetate and washed with 1M NaOH (×4), water (×2), then brine (×1), and dried over Na2SO4. Filtration, followed by removal of the solvent in vacuo, gave a residue that was purified via flash chromatography (1:4, ethyl acetate:hexanes, then 1:9 ethyl acetate:hexanes) to produce compound 105 (664 mg, 42% yield) as a colorless oil, 1H NMR (CDCl3, 300 MHz): 0.03 (s, 9H), 0.96-1.02 (m, 2H), 1.80-1.95 (m, 4H), 2.29 (bs, 2H), 2.59-2.64 (m, 2H), 3.46 (s, 2H), 4.15-4.29 (m, 4H), 7.21-7.30 (m, 5H); ESI(+)MS: 347 (M+H+).

Reference： [1]Patent: US2007/155715,2007,A1 .Location in patent: Page/Page column 20

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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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[ CAS No. 67571-90-8 ] {[proInfo.proName]}

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[ 67571-90-8 ] Synthesis Path-Upstream 1~4

[ 67571-90-8 ] Synthesis Path-Downstream 1~4

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