287114-25-4|tert-Butyl 8-azabicyclo[3.2.1]octan-3-ylcarbamate| Ambeed

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Quality Control of [ 287114-25-4 ] Purity: 98% SDS Specification

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Product Details of [ 287114-25-4 ]

CAS No. :	287114-25-4
Formula :	C₁₂H₂₂N₂O₂
M.W :	226.32
SMILES Code :	C12CCC(CC(C1)NC(OC(C)(C)C)=O)N2
MDL No. :	MFCD11045410
InChI Key :	UUHPKKKRSZBQIG-UHFFFAOYSA-N
Pubchem ID :	14774662

Safety of [ 287114-25-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of [ 287114-25-4 ]

* 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 [ 287114-25-4 ]

[ 287114-25-4 ] Synthesis Path-Downstream 1~35

1
(8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-carbamic acid tert-butyl ester [ No CAS ]
[ 287114-25-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; formic acid;palladium-carbon; In methanol;	Reference Example 17 3-(tert-Butoxycarbonylamino)-8-azabicyclo[3.2.1]octane 8-Benzyl-3-(tert-butoxycarbonylamino)-8-azabicyclo [3.2.1]octane was dissolved in 400 ml of methanol followed by adding formic acid (25.80 g) and 10% palladium carbon (5 g). The mixture was stirred at room temperature for 16 hours. Then, the catalyst was removed by filtration. The mother liquor was alkalized by adding an aqueous solution of sodium hydroxide, which was extracted with chloroform. The organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel (chloroform: methanol = 5:1) to provide brown oil (12 g).
	With sodium hydroxide; formic acid;palladium-carbon; In methanol;	Reference Example 17 3-(tert-Butoxycarbonylamino)-8-azabicyclo[3.2.1]octane 8-Benzyl-3-(tert-butoxycarbonylamino)-8-azabicyclo [3.2.1]octane was dissolved in 400 ml of methanol followed by adding formic acid (25.80 g) and 10% palladium carbon (5 g). The mixture was stirred at room temperature for 16 hours. Then, the catalyst was removed by filtration.The mother liquor was alkalized by adding an aqueous solution of sodium hydroxide, which was extracted with chloroform. The organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel (chloroform: methanol = 5:1) to provide brown oil (12 g).
	With hydrogen;palladium 10% on activated carbon; In ethanol; acetic acid; under 2068.65 Torr; for 6.0h;	The obtained crude solid material was transferred in a Parr vessel and diluted with ethanol (10 mL) and acetic acid (1.5 mL). 10% (w/w) Pd/C was added (300 mg). The hydrogenation was carried out at 40 psi. The reaction was completed after 6 h (TLC). The mixture was filtered through Celite. The obtained clear solution was concentrated in vacuo and azeotroped with toluene. After purification by flash chromatography (88:10:2 dichloromethane/methanol/28% (w/w) ammonium hydroxide), the title compound was obtained as an oil (106 mg), 77% yield over two steps. 1H NMR (400 MHz, CDCl3) δ 3.82 (br s, IH), 3.52 (br s, 2H), 2.09 (br s, 2H), 2.05 (m, 2H), 1.89 (m, 3H), 1.70 (d, J= 14 Hz, 2H), 1.44 (s, 9H); 13C NMR (100 MHz, CDCl3) δ 155.5, 53.6, 43.2, 37.9, 29.2, 28.6; MS (ESI+) for Ci2H22N2O2: 227 (MH+).

With hydrogen;palladium(II) hydroxide/carbon; In tetrahydrofuran; methanol; at 20℃; for 3.0h;

8g) 8-Aza-bicyclo[3.2.1]oct-3-yl)-carbamic acid tert-butyl esterTo a solution of Boc-protected amine (8f) (4.76 g) in THF (75ml) and methanol (75 ml) was added 20% Pd(OH)2 (3.17 g) . Thereaction mixture was stirred at room temperature under ahydrogen atmosphere for 3 hours. The catalyst was filtered offand the filtrate evaporated. The residue was purified by flashchromatography (silica gel, dichloromethane/methanol 9:1 + 1%ammonia) to give the desired product (3.29 g) .XH NMR (300MHz, CDC13) : 8: 4.57-4.45 (m, 1H) , 3.91-3.75 (m, 1H) ,3.61-3.52 (m, 2H), 2.93 (bs, 2H), 1.98-1.88 (m, 2H) , 1.87-1.68(m, 4H), 1.42-1.32 (m, 2H), 1.41 (s, 9H)

References: [1]Patent: EP1156045,2001,A1 .
[2]Patent: EP1243268,2002,A1 .
[3]Patent: WO2009/86264,2009,A1 .Location in patent: Page/Page column 239.
[4]Patent: WO2006/21448,2006,A1 .Location in patent: Page/Page column 42-43.

2
[ 287114-25-4 ]
[ 642478-13-5 ]
[ 877457-67-5 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium perchlorate; In N,N-dimethyl-formamide; at 20℃; for 120.0h;	78f) {8-[2-Hydroxy-2-(3-methoxy-quinoxalin-5-yl)-ethyl]-8-aza-bicyclo[3.2.1]oct-3-yl}-carbamic acid tert-butyl esterTo a solution of epoxide (78e) (179 mg) and amine (8g) (200 mg)in DMF (5 ml) was added lithium perchlorate (110 mg). Themixture was stirred for 5 days at room temperature. Water (70ml) was added and the mixture extracted with ethyl acetate. Thecombined organic layers were dried over magnesium sulfate,filtered and evaporated. The residue was purified by flashchromatography {silica gel, dichloromethane/methanol 19:1) togive the desired product {111 mg).1H NMR (300 MHz, CDC13) : 6: 8.50 (s, 1H) , 8.03-7.94 (m, 2H) ,7.64-7.58 (m, 1H), 5.80 (bd, 1H), 4.58-4.49 (m, 1H), 4.18 (s,3H) , 3.97-3.82 (m, 1H) , 3.77-3.65 (m, 1H), 3.45-3.35 (m, 1H),3.18-3.07 (m, 1H), 2.53-2.38 (m, 1H), 2.12-1.73 (m, 9H), 1.46(s, 9H)

References: [1]Patent: WO2006/21448,2006,A1 .Location in patent: Page/Page column 117-118.

3
[ 681278-32-0 ]
[ 287114-25-4 ]
[ 877457-34-6 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium perchlorate; potassium carbonate; In N,N-dimethyl-formamide; at 80℃;	8h) {8-[2-Hydroxy-2-(6-methoxy-[1,5]-naphthyridin-4-yl)-ethyl]-8-aza-bicyclo[3.2.1]oct-3-yl}-carbamic acid tert-butyl ester(enantiomer 1)2-Methoxy-8-oxiranyl-[1,5]-naphthyridine (If) (726 mg) and amine(8g) (813 mg) were dissolved in DMF (9 ml), treated withpotassium carbonate (521 mg) and lithium perchlorate (382 mg)and stirred at 80C over night. The mixture was concentrated,dissolved in dichloromethane/methanol 9:1 and washed with water.The organic layer was dried over magnesium sulfate, filtered andconcentrated. The residue was purified by flash chromatography(silica gel, dichloromethane/methanol 97:3) to give the desiredproduct (1.28 g).XH NMR (300MHz, d6-DMSO) : 5: 8.78 (d, 1H) , 8.26 (d, 1H) , 7.78(d, 1H), 7.28 (d, 1H), 6.69 (bs, 1H), 5.52 (bs, 1H), 4.03 (s,3H) , 3.65-3.52 (m, 2H) , 3.40-3.28 (m, 2H), 1.98-1.80 (m, 2H),1.72-1.43 (m, 6H) , 1.39-1.28 (m, 2H), 1.35 (s, 9H)

References: [1]Patent: WO2006/21448,2006,A1 .Location in patent: Page/Page column 43.

4
[ 287114-25-4 ]
[ 724788-18-5 ]
[ 877457-38-0 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium perchlorate; potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.666667h;Microwave apparatus;	25f) {8-[2-(3-Chloro-6-methoxy-[1,5]-naphthyridin-4-yl)-2-hydroay-ethyl]-8-aza-bicyclo[3.2.1]oct-3-yl}-carbamic acid tert-butyl esterEpoxide (25e) (200 mg) and amine (8g) (96 mg) were dissolved inDMF (2 ml), treated with potassium carbonate (61 mg) and lithiumperchlorate (45 mg) and heated in the microwave for 40 minutesat 130C. The mixture was concentrated, dissolved indichloromethane/methanol 9:1 and washed with water and brine.The organic layer was dried over magnesium sulfate, filtered andevaporated. The residue was purified by flash chromatography(silica gel, dichloromethane, dichloromethane/methanol 9:1 + 1%ammonia) to give the desired product (200 mg).MS (El): m/z: 463 [M+H]+

References: [1]Patent: WO2006/21448,2006,A1 .Location in patent: Page/Page column 65.

5
[ 287114-25-4 ]
[ 877457-45-9 ]
[ 877457-46-0 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium perchlorate; In N,N-dimethyl-formamide; at 80℃;	35g) {8-[2-Hydroxy-2-(3-methoxy-quinolin-5-yl)-ethyl]-8-aza-bicyclo[3.2.l]oct-3-yl}-carbamic acid tert-butyl ester(enantiomer 1)Epoxide (35f) (500 mg) was dissolved in DMF (13 ml), treatedwith amine (8g) (562 mg) and lithium perchlorate (317 mg) andstirred at 80C over night. The mixture was diluted with ethylacetate and washed with water and brine. The organic layer wasdried over magnesium sulfate, filtered and evaporated. Theresidue was purified by flash chromatography (silica gel,dichloromethane, dichloromethane/methanol 19:1) to give thedesired product (808 mg).^•H NMR (300 MHz, CDC13) : 5: 8.55 (d, 1H) , 7.90 (d, 1H) , 7.65-7.62(m, 2H), 7.48-7.43 (m, 1H), 5.66 (bs, 1H), 4.58 (bs, 1H), 3.85(s, 3H), 3.53-3.50 (m, 1H), 2.85-2.80 (m, 1H), 2.70-2.54 (m,1H) , 2.03-1.73 (m, 9H), 1.36 (s, 9H), 1.30-1.15 (m, 2H)

References: [1]Patent: WO2006/21448,2006,A1 .Location in patent: Page/Page column 78.

6
[ 287114-25-4 ]
[ 877457-57-3 ]
[ 877457-58-4 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium perchlorate; potassium carbonate; In N,N-dimethyl-formamide; at 140℃;	56g) {8-[2-(3-Chloro-6-methoxy-quinolin-4-yl)-2-hydroxy-ethyl]-8-aza-bicyclo[3.2.1]oct-3-yl}-carbamic acid tert-butyl ester(enantiomer 1)Epoxide (56f) (273 mg) and amine (8g) (262 mg) were dissolved inDMF (10 ml), treated with potassium carbonate (160 mg) andlithium perchlorate (129 mg) and stirred at 140C over night.The mixture was concentrated, dissolved indichloromethane/methanol 9:1 and washed with water. The organiclayer was dried over magnesium sulfate, filtered andconcentrated. The residue was purified by flash chromatography(silica gel, dichloromethane/methanol 19:1, 9:1) to give thedesired product (442 mg).^•H NMR (300 MHz, d6-DMSO) : 6: 8.64 (s, 1H) , 8.16 (d, 1H) , 7.93(d, 1H) , 7.42 (dd, 1H), 6.63 (d, 1H), 5.93 (bs, 1H), 5.57 (m,1H), 3.89 (s, 3H), 3.60-3.43 (m, 1H), 3.35-3.25 (m, 1H), 3.12-2.95 (m, 2H), 2.79-2.67 (m, 1H), 1.95-1.76 (m, 3H), 1.59-1.36(m, 5H), 1.35 (s, 9H)

References: [1]Patent: WO2006/21448,2006,A1 .Location in patent: Page/Page column 99.

7
[ 287114-25-4 ]
[ 877457-75-5 ]
[ 877457-78-8 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium perchlorate; In N,N-dimethyl-formamide; at 20℃; for 168.0h;	lOOa) {8-[2-(6-Chloro-3-methoxy-quinoxalin-5-yl)-2-hydroxy-ethyl]-8-aza-bicyclo[3.2.l]oct-3-yl}-carbamic acid tert-butylesterTo a solution of epoxide (93j) (708 mg) and amine (8g) (678 mg)in DMF (20 ml) was added lithium perchlorate (373 mg). Themixture was stirred for 7 days at room temperature. Water (150ml) was added and the mixture extracted with ethyl acetate. Thecombined organic layers were dried over magnesium sulfate,filtered and evaporated. The residue was purified by flashchromatography (silica gel, dichloromethane/methanol 19:1) togive the desired product (1.15 g).MS (El): m/z: 463 [M+H]+

References: [1]Patent: WO2006/21448,2006,A1 .Location in patent: Page/Page column 136.

8
[ 287114-25-4 ]
[ 1885-14-9 ]
8-Benzyloxycarbonyl-3-(tert-butoxycarbonylamino)-8-azabicyclo [3.2.1]octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium bicarbonate; triethylamine; In dichloromethane;	Reference Example 18 8-Benzyloxycarbonyl-3-(tert-butoxycarbonylamino)-8-azabicyclo [3.2.1]octane 3-(tert-Butoxycarbonylamino)-8-azabicyclo[3.2.1] octane (12 g) and triethylamine (5.93 g) were dissolved in 100 ml of methylenechloride, to which benzylchloroformate (9.99 g) was added dropwise under ice cooling. After stirring for 16 hours at room temperature, an aqueous saturated solution of sodium hydrogen carbonate was added to the reaction mixture, which was extracted with chloroform. The organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel (chloroform) to provide colorless oil (17 g).
	With sodium bicarbonate; triethylamine; In dichloromethane;	Reference Example 18 8-Benzyloxycarbonyl-3-(tert-butoxycarbonylamino)-8-azabicyclo[3.2.1]octane 3-(tert-Butoxycarbonylamino)-8-azabicyclo[3.2.1] octane (12 g) and triethylamine (5.93 g) were dissolved in 100 ml of methylene chloride, to which benzylchloroformate (9.99 g) was added dropwise under ice cooling. After stirring for 16 hours at room temperature, an aqueous saturated solution of sodium hydrogen carbonate was added to the reaction mixture,. which was extracted with chloroform. The organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel (chloroform) to provide colorless oil (17 g).

References: [1]Patent: EP1156045,2001,A1 .
[2]Patent: EP1243268,2002,A1 .

9
[ 287114-25-4 ]
[ 1361955-58-9 ]
[ 1363400-82-1 ]

References: [1]Letters in drug design and discovery,2011,vol. 8,p. 626 - 632.

10
[ 287114-25-4 ]
[ 1239707-73-3 ]
[ 1239893-92-5 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 4322 - 4335.

11
[ 287114-25-4 ]
[ 1239707-73-3 ]
C₃₁H₃₅Cl₄N₃O₄ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 4322 - 4335.

12
[ 287114-25-4 ]
[ 1373527-88-8 ]
C₃₂H₃₆Cl₂F₃N₃O₅ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 4322 - 4335.

13
[ 287114-25-4 ]
[ 1373527-90-2 ]
[ 1239893-94-7 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 4322 - 4335.

14
[ 287114-25-4 ]
[ 1373527-90-2 ]
C₃₁H₃₆BrCl₂N₃O₄ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 4322 - 4335.

15
[ 287114-25-4 ]
[ 1239707-78-8 ]
C₃₃H₃₈BrF₃N₂O₅ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 4322 - 4335.

16
[ 287114-25-4 ]
[ 1336911-04-6 ]
[ 1392889-06-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5326 - 5329.

17
[ 287114-25-4 ]
[ 1336911-04-6 ]
C₂₉H₃₈N₈O₂S [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5326 - 5329.

18
[ 287114-25-4 ]
{(endo)-8-[(S)-4-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl)-benzyl]-8-aza-bicyclo[3.2.1]oct-3-yl}-carbamic acid tert-butyl ester [ No CAS ]
(endo)-8-[(S)-4-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl)-benzyl]-8-aza-bicyclo[3.2.1]oct-3-ylamine dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In 1,4-dioxane; dichloromethane; at 25℃; for 24.0h;	Preparation of (endo)-8-[(S)-4-(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl)-benzyl]-8-aza-bicyclo[3.2.1]oct-3-ylamine dihydrochloride (O) To a solution of {(endo)-8-[(S)-4-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl)-benzyl]-8-aza-bicyclo[3.2.1]oct-3-yl}-carbamic acid tert-butyl ester (prepared from Intermediate C and (endo)-(8-aza-bicyclo[3.2.1]oct-3-yl)-carbamic acid tert-butyl ester according to General Method I) (285 mg, 0.568 mmol) in DCM (15 mL) was added 4M HCl in 1,4-dioxane (6.0 mL; 24.0 mmol) and the reaction stirred at about 25 C. for 24 hours. The reaction was concentrated and the solid suspended in DCM and heptane. Filter the solid to afford the title compound (Q).

References: [1]Patent: US2013/236468,2013,A1 .Location in patent: Paragraph 0319.

19
[ 287114-25-4 ]
C₂₀H₂₃NO₈S [ No CAS ]
C₃₁H₄₁N₃O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In acetonitrile; at 60℃;	[000255] A suspension of Compound A8 (1.00 g, 2.29 mmol mmol), tert-butyl-8-aza- bicyclo[3.2.1]octan-3-ylcarbamate (1.96 g, 6.86 mmol) and K2CO3 (1.58 g, 11.45 mmol) in ACN (30 mL) was stirred at 60 C overnight. The mixture was diluted with ethyl acetate (150 mL) and evaporated to give Compound El (1.20 g, yield 92%>) as a colorless oil. LCMS (m/z): 568 [M+l]+.

References: [1]Patent: WO2015/42397,2015,A1 .Location in patent: Paragraph 000255.

20
[ 287114-25-4 ]
N-(8-(5-chlorobenzo[d]oxazol-2-yl)-8-azabicyclo[3.2.1]octan-3-yl)-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide [ No CAS ]