[ CAS No. 280-13-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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Quality Control of [ 280-13-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 280-13-7 ]

SDS Specification

Alternatived Products of [ 280-13-7 ]

Product Details of [ 280-13-7 ]

CAS No. :	280-13-7	MDL No. :	MFCD09836264
Formula :	C₆H₁₁NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	POOPWPIOIMBTOH-UHFFFAOYSA-N
M.W :	113.16	Pubchem ID :	12069231
Synonyms :		Chemical Name :	8-Oxa-3-azabicyclo[3.2.1]octane

Safety of [ 280-13-7 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P261-P305+P351+P338	UN#:	1993
Hazard Statements:	H225-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 280-13-7 ]

* 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 [ 280-13-7 ]

[ 280-13-7 ] Synthesis Path-Downstream 1~14

1
[ 75-21-8 ]
[ 280-13-7 ]
[ 99969-71-8 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 393,395

2
[ 1472-00-0 ]
[ 280-13-7 ]

Reference： [1]Journal of the Chemical Society,1948,p. 155,157

3
[ 280-13-7 ]
[ 156478-71-6 ]
[ 666852-94-4 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 16h;	EDC (1.18g, 6.15 mmol) was added to a stirred solution of [N-BOC-PIPERAZINE] acetic acid [(L.] [OOG,] 4.10 mmol), 8-oxa-3-aza-bicyclo [3.2. 1. ] octane (0.556g, 4.92 mmol), 3-hydroxy benzotriazole (0.836g, 6.15 mmol), and diisopropylethylamine (2. 14ml, 12.31 mmol) in DCM (20 ml) at ambient temperature under nitrogen. After stirring for 16h the reaction was quenched by the addition of water [(20ML).] The phases were separated and the organics were washed with sat. brine [(20ML),] dried and evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica, eluting with 0-10% MeOH/DCM to give 46 as a white solid (0.780g). MS-ESI: 340 (M++H). [1H NMR (CDC13)] 1.45 (s, 9H), 1.80-2. 00 (m, 4H), 2.30-2. 58 (m, 4H), 2.85-3. 04 (m, [2H),] 3.25 (d, 1H), 3.30-3. 57 (m, 3H), 3.78 (d, 1H), 4.12 (d, 1H), 4.36 (d, 3H).

Reference： [1]Patent: WO2004/18480,2004,A1 .Location in patent: Page 103-104

4
[ 280-13-7 ]
[ 85-44-9 ]
[ 54746-03-1 ]

Yield	Reaction Conditions	Operation in experiment
	In benzene;	EXAMPLE 30 3-(o-Carboxybenzoyl)-8-Oxa-3-Azabicyclo(3.2.1)Octane SPC9 A solution of 11.3 grams (0.1 mole) 8-oxa-3-azabicyclo (3.2.1)octane in 20 ml of benzene was added to a suspension of 14.8 grams (0.1 mole) of phthalic anhydride in 50 ml of benzene at 8 C. The reaction mixture was stirred for 1 hour and then left overnight at room temperature. The product, 20.0 grams which separated, was filtered off and recrystallized from benzene ethanol. The product represented by formula (X) had a melting point of 149-150.5 C. Analysis for C14 H15 NO4. Calculated: C, 64.36%; H, 5.79%; N, 5.36%. Found: C, 64.38%; H, 5.85%; N, 5.24%.

Reference： [1]Patent: US3953596,1976,A

5
[ 280-13-7 ]
[ 5538-51-2 ]
3-(acetylsalicyloyl)-8-oxa-3-azabicyclo(3.2.1)octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In benzene;	EXAMPLE 29 3-(Acetylsalicyloyl)-8-Oxa-3-Azabicyclo(3.2.1)Octane SPC8 o-Acetoxybenzoyl chloride (0.1 mole, 19.85 grams) was slowly added to a mixture of 8-oxa-3-azabicyclo(3.2.1)octane (0.1 mole, 11.13 grams) and triethylamine (0.1 mole) in 60 ml of benzene at 20 C. The reaction mixture was stirred 2.5 hours at 25 C. The salt was filtered off and washed with benzene. After removal of benzene, the product was obtained as a viscous liquid which was purified by column chromatography (alumina). Impurities were eluted with ether and the product with methanol to yield the product represented by formula (IX). Analysis for C15 H17 NO4. Calculated: C, 65.44%; H, 6.23%; N, 5.09%. Found: C, 65.55%; H, 6.05%; N, 5.05%.

Reference： [1]Patent: US3953596,1976,A

6
[ 280-13-7 ]
[ 6601-22-5 ]
[ 1197160-15-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine; In water; acetone; at 20℃; for 6h;	To a stirred acetone/crushed ice suspension of 2,4-dichloro-6-morpholin-4-yl-[1,3,5]triazine (1.5 g, 6.5 mmol), 8-oxa-3-azabicyclo[3.2.1]octane (980 mg, 6.5 mmol) and triethylamine (3 ml) was added and stirred at room temperature for 6 h. At the end, the separated solid was filtered and washed with water. The crude product was found to be pure enough for further transformations. Yield: 2.0 g (99%); mp. 118; (M+H) 313.1.
99%	With triethylamine; In water; acetone; at 20℃; for 6h;	To a stirred acetone/crushed ice suspension of 2,4-dichloro-6-morpholin-4-yl-[1,3,5]triazine (1.5 g, 6.5 mmol), 8-oxa-3-azabicyclo[3.2.1]octane (980 mg, 6.5 mmol) and triethylamine (3 ml) was added and stirred at room temperature for 6 hours. At the end, the separated solid was filtered and washed with water. The crude product was found to be pure enough for further transformations. Yield: 2.0 g (99%); mp. 118; (M+H) 313.1

Reference： [1]Patent: US2009/291079,2009,A1 .Location in patent: Page/Page column 40
[2]Patent: US2017/119778,2017,A1 .Location in patent: Paragraph 0984

7
[ 280-13-7 ]
[ 16234-14-3 ]
[ 1144081-74-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 375 - 379

8
[ 280-13-7 ]
[ 1198277-84-7 ]
[ 1198277-93-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2259 - 2263
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2321 - 2325

9
[ 280-13-7 ]
[ 1144080-29-4 ]
[ 50270-27-4 ]
[ 1144080-35-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1440 - 1444

10
[ 280-13-7 ]
methyl [6-chloro-2-(methylsulfanyl)pyrimidin-4-yl](methylsulfonyl)acetate [ No CAS ]
[ 1233339-96-2 ]

Yield	Reaction Conditions	Operation in experiment
44%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 72h;	a) 8-oxa-3-azabicyclo[3.2.1]octane (627 mg, 5.54 mmol) was added to 4-chloro-6- (methylsulfonylmethyl)-2-(methylthio)pyrimidine (700 mg, 2.77 mmol) and DIPEA (1.447 mL, 8.31 mmol) in DCM (10 mL). The resulting mixture was stirred at rt for 3 days. The reaction mixture was washed sequentially with IM HCl (2 x 10 mL), water (10 mL) and saturated brine (10 mL). The organic layer was dried over MgSO4, filtered and then evaporated. The residue was purified by chromatography on silica eluting with a gradient of 0 to 10% MeOH in DCM. Pure fractions were combined and evaporated to afford 3-(6- (methylsulfonylmethyl)-2-(methylthio)pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1 Joctane (400 mg, 44%); m/z: (ESI+) MH+, 330.06.

Reference： [1]Patent: WO2010/73034,2010,A1 .Location in patent: Page/Page column 100
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 2125 - 2138

11
[ 280-13-7 ]
[ 1226854-16-5 ]
[ 1198278-01-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2321 - 2325

12
[ 280-13-7 ]
[ 1198278-07-7 ]
[ 1226854-18-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2321 - 2325

13
[ 280-13-7 ]
[ 4359-87-9 ]
[ 1250867-75-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine; In dichloromethane; at 0 - 20℃;	2,4,6-Trichloro-5-nitropyrimidine (45, 1.43 g, 6.26 mmoles) was dissolved in dichloromethane and cooled to 0 C. A solution of 8-oxa-3-azabicyclo[3.2.1]octane (2, 0.934 g, 6.26 mmoles) in dichloromethane and triethylamine (0.873 ml_, 6.26 mmoles) was slowly added over 1 hour. The solution was allowed to stir at 0 C for 2 hours, then warmed to room temperature and stirred for an additional 16 hours. The reaction mixture was filtered, the filtrate was concentrated, dissolved in ethyl acetate, washed with 1 N hydrochloric acid, saturated sodium bicarbonate, brine, dried, and concentrated to provide 3-(2,6-dichloro-5-nitropyrimidin-4- yl)-8-oxa-3-azabicyclo[3.2.1]octane (46). Yield: 1.53 g (80%). HRMS; [M+H]+ Obs'd = 305.0200, [M+H]+ Calc'd = 305.0203.

Reference： [1]Patent: WO2010/120998,2010,A1 .Location in patent: Page/Page column 75

14
[ 280-13-7 ]
2,4-dichloro-6-[(methylsulfonyl)methyl]pyrimidine [ No CAS ]
[ 1250867-57-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine; In dichloromethane; at 0℃;Reflux;	A 2,4-dichloro-6-(methylsulfonylmethyl)pyrimidine (42, prepared as reported inWO2008/023159, 1.6O g, 6.64 mmoles) was dissolved in dichloromethane and cooled to 0 0C. A solution of 8-oxa-3-azabicyclo[3.2.1]octane (2, 0.990 g, 6.64 mmoles) in dichloromethane and triethylamine (1.94 ml_, 13.94 mmoles) was slowly added over 15 minutes. The solution was allowed to warm to room temperature over 30 minutes then heated to reflux for 1.5 hours. The reaction mixture was stirred at room temperature for an additional 18 hours, then concentrated and purified by chromatography on silica gel (eluting with 2-3% methanol in dichloromethane) to provide 3-(2-chloro-6-(methylsulfonylmethyl)pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1 ]octane (43) as a white solid. Yield: 1.72 g (82%). HRMS; [M+H]+ Obs'd = 318.0669, [M+H]+ Calc'd = 318.0674

Reference： [1]Patent: WO2010/120998,2010,A1 .Location in patent: Page/Page column 49; 73

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Technical Information

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Code	Phrase
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
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H200	Unstable explosive
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
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H290	May be corrosive to metals
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H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
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H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 280-13-7 ] {[proInfo.proName]}

Quality Control of [ 280-13-7 ]

Related Doc. of [ 280-13-7 ]

Product Details of [ 280-13-7 ]

Safety of [ 280-13-7 ]

Application In Synthesis of [ 280-13-7 ]

[ 280-13-7 ] Synthesis Path-Downstream 1~14

Technical Information

Similar Product of [ 280-13-7 ]

Related Parent Nucleus of [ 280-13-7 ]

Other Aliphatic Heterocycles

Precautionary Statements-General

Prevention

Response

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[ 280-13-7 ]

Related Parent Nucleus of
[ 280-13-7 ]