1127-13-5|4-Hydroxybicyclo[2.2.2]octane-1-carboxylic acid| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 1127-13-5 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 1127-13-5 ]

CAS No. :	1127-13-5
Formula :	C₉H₁₄O₃
M.W :	170.21
SMILES Code :	O=C(C1(CC2)CCC2(O)CC1)O
MDL No. :	MFCD00102273
InChI Key :	LXQJPKMORWPZGM-UHFFFAOYSA-N
Pubchem ID :	12560136

Safety of [ 1127-13-5 ]

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

Application In Synthesis of [ 1127-13-5 ]

* 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 [ 1127-13-5 ]

[ 1127-13-5 ] Synthesis Path-Downstream 1~35

1
[ 92017-20-4 ]
[ 1127-13-5 ]

References: [1]Journal of the American Chemical Society,1953,vol. 75,p. 637,639.

2
[ 72948-78-8 ]
[ 1127-13-5 ]

References: [1]Helvetica Chimica Acta,1979,vol. 62,p. 2802 - 2816.
[2]Chemistry - A European Journal,2019,vol. 25,p. 14010 - 14014.

3
[ 23062-51-3 ]
[ 1127-13-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With hydrogenchloride; water; at 100℃; for 24h;	To a 500-mL round-bottom flask was added methyl 4-bromobicyclo[2.2.2]octane-l- carboxylate 58e (24.7 g, 99.95 mmol, 1.0 equiv.) and HCi (aq., 10%, 250 mL). The resulting mixture was stirred for 24h at 100 C. After cooling to RT, the pH value of the solution was adjusted to 3.0 using a HCi (6 M) solution. The aqueous mixture was extracted with ethyl acetate (400 mL x 3), and the combined organic layers were dried over anhydrous sodium sulfate, concentrated in vacuo to afford 4-hydroxybicyclo[2.2.2]octane-l-carboxylic acid 58d (15.5 g, 91%) as a light yellow solid.
89%		To the title compound from the Preparative Example 55, Step A (677 mg) was added 10% aqueous NaOH (65 niL). The mixture was stirred at 100C (temperature of the oil bath) for 42 h, concentrated to 15 mL and diluted with IN aqueous HCl (3O mL). The resulting mixture was acidified to pH 1 with 12N aqueous HCl and extracted with EtOAc (5 x 70 mL). The combined organic phases were dried (MgSO4), filtered and concentrated to afford the title compound (540 mg, 89%). [MH]+ = 171
		Preparation of Bicyclic Amine Intermediate 20 (BAI-20)4-hydroxybicyclo[2.2.2]octane-1-carboxylic acid Methyl 4-bromobicyclo[2.2.2]octane-1-carboxylate (BAI-19, 0.246 g, 0.001 mol) was refluxed in 25 mL of 1% sodium hydroxide solution for 24 hours. After cooling, the reaction solution was acidified with 6 N hydrochloric acid and extracted with ether (50 mL×6). The combined ether layers were dried over magnesium sulfate and concentrated to small volume. Recrystallization from n-hexane and diethyl ether (40:10 mL) gave the titled compound. 1H NMR (400 MHz, DMSO-d6) delta ppm 1. 1.68-1.78 (m, 6H), 1.48-1.52 (m, 6H), 4.00 (s, 1H), 12.00 (s, 1H).

		Methyl 4- bromobicyclo [2.2.2]octane-l-carboxylate (17.0 g, 69.0 mol) was refluxed in aqueous sodium hydroxide solution (1500 mL, 1 %) for 24 h. After cooling, the reaction solution was acidified with hydrochloric acid (6 N, 100 mL) and extracted with diethyl ether (6 x 500 mL). The combined ether layers were dried over magnesium sulfate and concentrated to afford the title compound (10.4 g, 61.1 mmol, 89 % yield), which was used in the next step without further purification. MS (ESI) m/z 169.2 [M-H]~.
110 mg		A mixture of methyl 4-bromobicyclo[2.2.2]octane-l-carboxylate (183 mg, 0.741 mmol) and 0.25 M sodium hydroxide (15 mL, 3.75 mmol) in a seal tube was heated in an oil bath at 100 C for 24 h. The mixture was extracted with ether and the separated aqueous phase was chilled with an ice bath, acidified with 2 M HCl to pH 3 and extracted with EtOAc (20 mL, X3). The combined organic layers were washed with brine, dried over MgSC^, filtered and evaporated to afford Cap W-21 (1 10 mg) as a white solid. 1H NMR (500MHz, DMSO-d6) delta 1 1.97 (br. s., 1H), 4.29 (s, 1H), 1.98 - 1.65 (m, 6H), 1.61 - 1.36 (m, 6H).

References: [1]Patent: WO2018/39384,2018,A1 .Location in patent: Paragraph 00512.
[2]Patent: WO2006/128184,2006,A2 .Location in patent: Page/Page column 174.
[3]Journal of Organic Chemistry,1970,vol. 35,p. 917 - 923.
[4]Patent: US2010/267738,2010,A1 .Location in patent: Page/Page column 34.
[5]Patent: WO2012/145569,2012,A1 .Location in patent: Page/Page column 136.
[6]Patent: WO2015/5901,2015,A1 .Location in patent: Page/Page column 609.

4
[ 1127-13-5 ]
[ 74-88-4 ]
[ 773-34-2 ]

References: [1]Journal of the American Chemical Society,1964,vol. 86,p. 5183 - 5188.

5
5,6-diamino-1-propyl-1H-pyrimidine-2,4-dione hydrochloride [ No CAS ]
[ 1127-13-5 ]
C₁₆H₂₄N₄O₄ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7132 - 7139.

6
[ 1659-95-6 ]
[ 1127-13-5 ]

References: [1]Journal of Organic Chemistry,1970,vol. 35,p. 917 - 923.

7
[ 1659-67-2 ]
[ 1127-13-5 ]

References: [1]Journal of Organic Chemistry,1970,vol. 35,p. 917 - 923.

8
[ 100-21-0 ]
[ 1127-13-5 ]

References: [1]Journal of Organic Chemistry,1970,vol. 35,p. 917 - 923.

9
[ 1459-96-7 ]
[ 1127-13-5 ]

References: [1]Journal of Organic Chemistry,1970,vol. 35,p. 917 - 923.
[2]Patent: WO2015/5901,2015,A1 .
[3]Patent: WO2012/145569,2012,A1 .

10
[ 18720-35-9 ]
[ 1127-13-5 ]

References: [1]Journal of Organic Chemistry,1970,vol. 35,p. 917 - 923.
[2]Patent: WO2015/5901,2015,A1 .
[3]Patent: WO2012/145569,2012,A1 .
[4]Patent: WO2018/39384,2018,A1 .

11
[ 1659-96-7 ]
[ 1127-13-5 ]

References: [1]Journal of Organic Chemistry,1970,vol. 35,p. 917 - 923.

12
[ 72948-77-7 ]
[ 1127-13-5 ]

References: [1]Helvetica Chimica Acta,1979,vol. 62,p. 2802 - 2816.
[2]Chemistry - A European Journal,2019,vol. 25,p. 14010 - 14014.

13
[ 1127-13-5 ]
[ 66789-33-1 ]

References: [1]Helvetica Chimica Acta,1979,vol. 62,p. 2802 - 2816.

14
[ 1127-13-5 ]
[ 18107-18-1 ]
[ 23062-53-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	In methanol; hexane; at 20℃; for 2h;	To a solution of 4-hydroxy-bicyclo [2. 2. 2] OCTANE-1-CARBOXYLIC acid (0. 10 g, 0. 59 mmol) in methanol (5 mL), was slowly added a solution of (trimethylsilyl) diazomethane in hexane (2. 0 M, 1 mL). The reaction mixture was stirred for 2 hours at room temperature. Solvent was then removed to give 4-hydroxy- bicyclo [2. 2. 2] octane-1-carboxylic acid methyl ester as a yellow solid (0. 105 g, 99%). H NMR (300 MHz, CDC13, 5) : 3. 56 (s, 3H), 1. 85 (m, 6H), 1. 59 (m, 6H).
89%	In methanol; dichloromethane; at 20℃;	To a 500 mL round-bottom flask was added 4-hydroxybicyclo[2.2.2]octane-l-carboxylic acid 58d (15.5 g, 91.07 mmol, 1.0 equiv.), dichloromethane (85 mL), methanol (45 mL), and TMSCHN2 (85 mL, 2.0 equiv.). The resulting mixture was stirred overnight at RT, then concentrated in vacuo. The crude product was purified by Flash-Prep-HPLC using the following conditions: Column, silica gel; mobile phase, PE:EtOAc = 100:0 increasing to PE:EtOAc =:: 90: 10 within 20 min; Detector, UV 254 nm, yielding methyl 4-hydroxybicyclo[2.2.2]octane-l- carboxylate 58e (15 g, 89%) as a white solid.

References: [1]Patent: WO2004/72033,2004,A2 .Location in patent: Page 40-41.
[2]Patent: WO2018/39384,2018,A1 .Location in patent: Paragraph 00513.

15
5,6-diamino-1-propyl-1H-pyrimidine-2,4-dione hydrochloride [ No CAS ]
[ 1127-13-5 ]
8-(4-hydroxybicyclo[2.2.2]oct-1-yl)-3-propyl-3,7-dihydropurine-2,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In water; N,N-dimethyl-formamide;	Step 2: 8-(4-Hydroxy-bicyclo[2.2.2]oct-1-yl)-3-propyl-3,7-dihydro-purine-2,6-dione 5,6-Diamino-1-propyl-1H-pyrimidine-2,4-dione hydrochloride salt (3.4 g) was dissolved in 80 mL of DMF along with <strong>[1127-13-5]4-hydroxy-bicyclo[2.2.2]octane-1-carboxylic acid</strong> (2.5 g, 15 mmol). HATU (5.9 g, 1.05 eq) was added, followed by Et3N (8.30 mL, 4.05 eq). The resulting reaction mixture was stirred at rt overnight. The teaction mixture was filtered to remove some of the precipitate. The filtrate was concentrated under reduced pressure. The resulting residue was dissolved in 60 mL of H2O containing 10 eq of NaOH (5.9 g). The reaction mixture was stirred under reflux for 1 h, cooled to rt and acidified to pH2 with concentrated HCl. The resulting precipitate was collected by filtration and dried to afford 1.85 g of the xanthine derivative.

References: [1]Patent: US2002/111333,2002,A1 .

16
[ 1127-13-5 ]
[ 72948-86-8 ]

Yield	Reaction Conditions	Operation in experiment
90%		To a cooled (-300C) solution of the title compound from the Preparative Example 81, Step A (540 mg) and NEt3 (590 muL) in THF (35 mL) was added ethyl chloroformate (320 muL). The mixture was stirred at -30C for 1 h and then filtered. The precipitated salts were washed with THF (20 mL). The combined filtrates were cooled to -20C and a 33% solution Of NH3 in H2O (10 mL) was added. The mixture was stirred at -2O0C for 20 min, then the cooling bath was removed and the mixture was stirred at room temperature for 40 min. The mixture was concentrated and dissolved in THF/CH3CN (4:1, 25 mL). Pyridine (1.26 mL) was added and the mixture was cooled to O0C. Trifluoroacetic anhydride (1.10 mL) was added and the mixture was stirred at O0C for 2 h. Then the mixture was concentrated to 5 mL, diluted with MeOH (18 mL) and 10% aqueous K2CO3 (9 mL), stirred at room temperature overnight, concentrated to 10 mL, acidified to pH 1 with IN aqueous HCl and extracted with CH2Cl2 (4 x 75 mL). The combined organic phases were dried (MgSO4), filtered, concentrated and purified by chromatography (silica, CH2Cl2/Me0H) to afford the title compound (433 mg, 90%). [MH]+ = 152.

References: [1]Patent: WO2006/128184,2006,A2 .Location in patent: Page/Page column 175.

17
[ 1127-13-5 ]
[ 75-65-0 ]
[ 1252672-84-6 ]

Yield	Reaction Conditions	Operation in experiment
	With diphenyl phosphoryl azide; triethylamine; In 1,4-dioxane; at 80℃;	Preparation of Bicyclic Amine Intermediate 21 (BAI-21) tent-butyl (4-hydroxybicyclo[2.2.2]oct-1-yl)carbamateTo a solution of <strong>[1127-13-5]4-hydroxybicyclo[2.2.2]octane-1-carboxylic acid</strong> (BAI-20, 340 mg, 2 mol) in dioxane (5 mL) was added triethylamine (202 m g, 2 mmol), diphenyl phosphoryl azide (550 mg, 2 mmol) and tent-butanol (3 g, 40 mmol). The reaction mixture was stirred for 45 minutes at 80 C. overnight. Then the mixture was concentrated under reduced pressure. The residue was dissolved in 30 mL of ethyl acetate and then washed with saturated NaHCO3 and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated to afford the crude titled compound which was used in the next step without further purification.

References: [1]Patent: US2010/267738,2010,A1 .Location in patent: Page/Page column 34.

18
[ 1127-13-5 ]
[ 100-51-6 ]
[ 1403864-73-2 ]

Yield	Reaction Conditions	Operation in experiment
	With diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 80℃;	To a solution of 4-hydroxybicyclo[2.2.2]octane-l-carboxylic acid (10.4 g, 61.1 mmol) in dioxane (150 mL) was added DIEA (11.8 g, 91.5 mmol), diphenyl phosphoryl azide (25 g, 91.5 mmol) and benzyl alcohol (131 g, 1.22 mol). The mixture was stirred at 80 C overnight. Then the reaction was concentrated under reduce pressure to remove dioxane and benzyl alcohol (100 C, 2 mm Hg). The residue was purified by silica gel column chromatography (5 % methanol in DCM) to give the title product (15.4 g, 54 mmol, yield 91%). 1H NMR(400 MHz, CDC13) delta ppm 7.35-7.30 (m, 5H), 5.03 (s. 2H), 4.55 (br s, 1H), 2.01-1.95 (m, 6H), 1.77-1.72 (m, 6H); MS (ESI) m/z 276.3 [M+H]+.

References: [1]Patent: WO2012/145569,2012,A1 .Location in patent: Page/Page column 136.

19
[ 619-81-8 ]
[ 1127-13-5 ]

References: [1]Patent: WO2012/145569,2012,A1 .

20
[ 106004-06-2 ]
[ 1127-13-5 ]

References: [1]Patent: WO2012/145569,2012,A1 .

21
[ 94-60-0 ]
[ 1127-13-5 ]

References: [1]Patent: WO2012/145569,2012,A1 .

22
[ 1403864-72-1 ]
[ 1127-13-5 ]

References: [1]Patent: WO2012/145569,2012,A1 .
[2]Patent: WO2018/39384,2018,A1 .

23
[ 1127-13-5 ]
C₁₆H₃₀O₃Si [ No CAS ]