280-13-7|8-Oxa-3-azabicyclo[3.2.1]octane| Ambeed

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Quality Control of [ 280-13-7 ] Purity: 98% SDS Specification

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Product Details of [ 280-13-7 ]

CAS No. :	280-13-7
Formula :	C₆H₁₁NO
M.W :	113.16
SMILES Code :	C1CC2CNCC1O2
MDL No. :	MFCD09836264
InChI Key :	POOPWPIOIMBTOH-UHFFFAOYSA-N
Pubchem ID :	12069231

Safety of [ 280-13-7 ]

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

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 1~35

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

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

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

References: [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).

References: [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%.

References: [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%.

References: [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

References: [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 ]

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

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

References: [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 ]

References: [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.

References: [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 ]

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

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

References: [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.

References: [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

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

15
[ 280-13-7 ]
2-chloro-9-hydroxy-1,9a-dihydropyrido[1,2-a]pyrimidin-4-one [ No CAS ]
9-hydroxy-2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrido[1,2-a]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In ethanol; at 120℃; for 2h;Microwave irradiation;	2-chloro-9-hydroxy-1 ,9a-dihydropyrido[1 ,2-a]pyrimidin-4-one (Y2, 383 mg, 1.95 mmol), N- ethyl-N-isopropylpropan-2-amine (0.407 mL, 2.34 mmol) and (8-oxa-3- azabicyclo[3.2.1]octane (350 mg, 2.34 mmol) were dissolved in ethanol (10 mL) and sealed into a microwave tube. The reaction was heated to 1500C for 2 hours in the microwave reactor and cooled to room temperature. The reaction mixture was filtered then purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford θ-hydroxy^δ-oxa-S-azabicycloβ^.iloctan-S-yOpyridoϖ ^-alpyrimidin^-one (270 mg, 50.7 %) as a white solid; 1H NMR (400 MHz, DMSO) δ 1.75 (4H, ddd), 3.01 (2H, d), 4.21 (2H, br s), 4.41 (2H, d), 5.49 (1 H, s), 6.93 (1H, t), 7.12 (1 H, dd), 8.29 (1 H, dd), 9.47 (1 H, s); m/z: 274.07 (MH+).

References: [1]Patent: WO2010/136778,2010,A1 .Location in patent: Page/Page column 75-76.

16
[ 280-13-7 ]
[ 1260089-81-3 ]
[ 1260089-85-7 ]

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 3426 - 3435.

17
[ 280-13-7 ]
[ 1313026-83-3 ]
[ 1313026-63-9 ]

Yield	Reaction Conditions	Operation in experiment
51%	With triethylamine; In ISOPROPYLAMIDE; for 0.5h;microwave irradiation;	To a solution of 5-(2-chloro-9-/sopropyl-9H-purin-6-yl)-pyrazin-2-ylamine (0.46 g, 1.60 mmol) dissolved in 15 ml. of DMA was added 8-oxa-3-aza- bicyclo[3.2.1]octane (0.81 g, 7.19 mmol) and 7 mL of triethyamine. The brown solution was heated using microwave irradiation for 30 minutes. The reaction mixture was dissolved in H2O and ethyl acetate and the organic layer was separated. The aqueous layer was extracted twice with ethyl acetate. Purification by flush column chromatography (silica gel, 2% of methanol in DCM) afforded 5-[9-/sopropyl-2-(8-oxa- 3-aza-bicyclo[3.2.1]oct-3-yl)-9H-purin-6-yl]-pyrazin-2-ylamine (51% yield) as a brown solid. 1H NMR CDCI3 (ppm): 9.21 (d, 1H), 8.25 (d, 1H), 7.88 (s, 1H), 4.84 (s, 2H), 4.74-4.82 (septet, 1H), 4.51 (m, 2H), 3.26-3.30 (dd, 4H), 1.87-1.97 (m, 4H), 1.59-1.60 (d, 6H). m/z: 367.22 [MH+]

References: [1]Patent: WO2011/78795,2011,A1 .Location in patent: Page/Page column 73.

18
[ 280-13-7 ]
[ 1339891-28-9 ]
[ 1339891-88-1 ]

Yield	Reaction Conditions	Operation in experiment
49%	With potassium tert-butylate;tris-(dibenzylideneacetone)dipalladium(0); XPhos; In tetrahydrofuran; at 40℃; for 11h;Inert atmosphere;	Example 583-(4-(7-(4-(8-Oxa-3-azabicvclo[3.2.11octan-3-yl)phenyl)imidazori,2-c1pyrimidin-5-yl)-lH- pyrazol- -yl)-3 -cyclopropylpropanenitrile[00700] Preparation of 3 -(4-(5 -(1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-Pyrazol-4-yl)imidazo[l ,2-c1pyrimidin-7-yl)phenyl)-8-oxa-3-azabicvclo[3.2.11octane: To a flask charged with 7-(4-bromophenyl)-5-(l-((2-(trimethylsilyl)ethoxy)methyl)-lH-pyrazol-4- yl)imidazo[l,2-c]pyrimidine (Preparation L; 0.250 g, 0.531 mmol), 8-oxa-3- azabicyclo[3.2.1]octane (0.430 g, 3.80 mmol), and potassium 2-methylpropan-2-olate (0.1 19 g, 1.06 mmol) was added 6 mL of THF at ambient temperature with stirring. Argon was bubbled through the reaction for 10 minutes before dicyclohexyl(2',6'-dimethoxybiphenyl-2- yl)phosphine (0.0436 g, 0.106 mmol) and tris(dibenzylideneacetone)dipalladium (0.0487 g, 0.0531 mmol) were added. Argon was bubbled through the reaction for 15 minutes before the reaction was sealed and allowed to proceed at 40 C for 4 hours. The reaction was charged with more tris(dibenzylideneacetone)dipalladium (0.0487 g, 0.0531 mmol) and purged with argon for 5 minutes before it was sealed and allowed to proceed at 40 C for 7 hours. The reaction mixture was diluted with DCM and aqueous saturated sodium bicarbonate (2 mL) and stirred for 30 minutes. The layers were separated and the organic layer was dried over MgSO i, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography eluting with 1% methanol in DCM to afford 3 -(4-(5 -( 1 -((2-(trimethylsilyl)ethoxy)methyl)- 1 H-pyrazol-4-yl)imidazo [ 1 ,2- c]pyrimidin-7-yl)phenyl)-8-oxa-3-azabicyclo[3.2.1]octane (0.133 g, 0.265 mmol, 49.0% yield). MS (apci) m/z = 503.2 (M+H).

References: [1]Patent: WO2011/130146,2011,A1 .Location in patent: Page/Page column 125.

19
[ 280-13-7 ]
[ 1352076-83-5 ]
[ 1352065-32-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane;	To a solution of 2-((3R,5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxo- l-((S)-l-oxobutan-2-yl)piperidin-3-yl)acetic acid (99 mg, 0.215 mmol; Example 210, Step A) in DCE (3 mL) was added 48.7 mg (0.43 mmol) of 8-oxa-3-azabicyclo[3.2.1]octane(Connolly, T.; Considine, J.; Ding, Z.; Forsatz, B.; Jennings, M.; MacEwan, M.; McCoy, K.; Place, D.; Sharma, A.; Sutherland, K. Organic Process Research & Development. 2010,14(2), 459-465. Note: reference is for the HC1 Salt). Sodium triacetoxyborohydride (91 mg, 0.430 mmol) was added followed by acetic acid (1.2 μΕ, 0.022 mmol). After stirring overnight, the mixture was partitioned between 5% aq. HC1 and ethyl acetate. The organic layer was washed with sat. aq. NaCl solution, dried over Na2S04, and concentrated. The residue was purified by reversed phase preparatory HPLC (eluent: 0-100% MeCN +0.1% TFA in water + 0.1% TFA, over 20 minutes). Fractions containing the product were transferred to a separatory funnel and sat. aq. NaHCOs and dichloromethane were added. The aqueous layer was back extracted with dichloromethane. The combined organic layers were washed with sat. aq. NaCl solution, dried over anhydrous Na2S04, filtered and the filtrate was concentrated to afford the title compound. 1H NMR (400 MHz, CHLOROFORM-;/) δ ppm 0.37 - 0.53 (m, 3 H) 1.48 - 1.58 (m, 4 H) 1.83 - 2.15 (m, 7 H) 2.18 - 2.31 (m, 2 H) 2.50 (s, 2 H) 2.60 (d, J=10.76 Hz, 1 H) 2.70 (d, J=15.65 Hz, 1 H) 2.96 - 3.17 (m, 4 H) 4.29 - 4.42 (m, 2 H) 4.55 (d, J=10.56 Hz, 1 H) 6.65 (dt, J=7.68, 1.44 Hz, 1 H) 6.94 - 7.02 (m, 1 H) 7.06 - 7.13 (m, 1 H) 7.14 - 7.21 (m, 1 H) 7.21 - 7.33 (m, 4 H). Mass Spectrum (ESI) m/z = 559.2 (M+l).

References: [1]Patent: WO2011/153509,2011,A1 .Location in patent: Page/Page column 502-503.

20
[ 280-13-7 ]
[ 1374986-81-8 ]