171361-65-2|Ethyl 1-oxaspiro[2.5]octane-6-carboxylate| Ambeed

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Quality Control of [ 171361-65-2 ] Purity: 95% SDS Specification

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Product Details of [ 171361-65-2 ]

CAS No. :	171361-65-2
Formula :	C₁₀H₁₆O₃
M.W :	184.23
SMILES Code :	CCOC(=O)C1CCC2(CO2)CC1
MDL No. :	MFCD12498695
InChI Key :	GQJWTOYPOHWVKC-UHFFFAOYSA-N
Pubchem ID :	45588272

Safety of [ 171361-65-2 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H311-H331
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501
Class:	6.1
UN#:	2810
Packing Group:	Ⅲ

Application In Synthesis of [ 171361-65-2 ]

* 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 [ 171361-65-2 ]

[ 171361-65-2 ] Synthesis Path-Downstream 1~35

1
[ 186581-53-3 ]
[ 17159-79-4 ]
[ 122898-08-2 ]
[ 171361-65-2 ]
[ 171361-62-9 ]
ethyl 4-oxocyclooctanecarboxylate [ No CAS ]

References: [1]Tetrahedron,1995,vol. 51,p. 10259 - 10280.
[2]Tetrahedron,1995,vol. 51,p. 10259 - 10280.

2
[ 17159-79-4 ]
[ 18107-18-1 ]
[ 122898-08-2 ]
[ 171361-65-2 ]
[ 171361-62-9 ]
ethyl 4-oxocyclooctanecarboxylate [ No CAS ]

References: [1]Tetrahedron,1995,vol. 51,p. 10259 - 10280.
[2]Tetrahedron,1995,vol. 51,p. 10259 - 10280.
[3]Tetrahedron,1995,vol. 51,p. 10259 - 10280.

3
[ 22013-33-8 ]
[ 171361-65-2 ]
[ 1010814-77-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	In ethanol; water;Heating / reflux;	A solution of l-oxa-spiro[2.5]octane-6-carboxylic acid ethyl ester obtained according to Tetrahedron, 1995, 51, 10259-80, (4.5 g, 24.4 mmol) and 2,3-dihydro-benzo[l,4]dioxin- 6-ylamine (3.7 g, 24.4 mmol) in EtOH/water (9:1, 100 ml) was heated at reflux overnight. The mixture was concentrated in vacuo and purified by chromatography (Hex:EA 2:1) to give the title amino alcohols (7.7 g, 94% yield) as an orange oil.1H NMR (DMSO d6) delta: 6.60-6.50 (m, IH); 6.20-6.10 (m, 2H); 5.90-5.70 (m, IH); 4.10-3.90 (m, 6H); 3.90-3.80 (m, 2H); 2.40-2.20 (m, IH); 1.80-1.40 (m, 7H), 1.40-1.20 (m, 2H); 1.10-1.00 (m, 4H).

References: [1]Patent: WO2008/26172,2008,A1 .Location in patent: Page/Page column 56.

4
[ 62-53-3 ]
[ 171361-65-2 ]
[ 1044271-29-5 ]

Yield	Reaction Conditions	Operation in experiment
	In tert-butyl alcohol; at 150℃; for 1h;Microwave irradiation;	Intermediate 8; Ethyl 4-hvdroxy-4-r(phenylamino)methyllcvclohexanecarboxylate; Ethyl 1-oxaspiro[2.5]octane-6-carboxylate (Intermediate 9 procedure 9a, 704.5 mg, 3.82 mmol) was dissolved in t-BuOH (4ml) and aniline (697 mul, 7.65 mmol, Aldrich) was added. The reaction was stirred and heated at 1500C under microwave irradiation for two 30 minute cycles. The mixture was poured into a saturated aqueous solution of NH4CI and extracted with ethyl acetate; the organic phase was dried on Na2SO4, filtered and <n="29"/>evaporated in vacuo to give crude ethyl 4-hydroxy-4-[(phenylamino)methyl]- cyclohexanecarboxylate (1.19 g), which was used without further purification. Another batch of the same compound was prepared using an analogous method showed the following NMR spectra: 1H NMR (400 MHz, CDCI3): delta 7.14-7.24 (2H, m), 6.65-6.77 (3H, m), 4.10-4.20 (2H, m), 3.16-3.21 (1 H, m), 3.09-3.13 (1 H, m), 2.45-2.54 (1 H, m), 2.23-2.34 (1 H, m), 1.36-2.02 (9H, m), 1.22-1.30 (3H, m). cis/trans 65:35
	In tert-butyl alcohol; at 150℃; for 1h;Microwave irradiation;	Intermediate 7: Ethyl 4-hvdroxy-4-[(phenylamino)methyl1cvclohexanecarboxvlate; <n="33"/>Ethyl 1-oxaspiro[2.5]octane-6-carboxylate (Intermediate 8, 704.5 mg, 3.82 mmol) was dissolved in t-BuOH (4 ml) and aniline (697 mul, 7.65 mmol, commercially available from e.g. Aldrich) was added. The reaction was stirred and heated at 150 0C under microwave irradiation for two 30 minute cycles. The mixture was poured into a saturated aqueous solution of NH4CI and extracted with EtOAc; the organic phase was dried on Na2SC>4, filtered and evaporated in vacuo to give crude ethyl 4-hydroxy-4- [(phenylamino)methyl]cyclohexanecarboxylate (1.19 g), which was used without further purification. Another batch of the same compound prepared using an analogous method gave, 1 H-NMR (400 MHz, CDCI3): delta 1.22-1.30 (m, 3 H), 1.36-2.02 (m, 9 H), 2.23-2.34 (m, 1 H), 2.45-2.54 (m, 1 H), 3.09-3.13 (m, 1 H), 3.16-3.21 (m, 1 H), 4.10-4.20 (m, 2 H), 6.65- 6.77 (m, 3 H), 7.14-7.24 (m, 2 H).

References: [1]Patent: WO2008/92887,2008,A1 .Location in patent: Page/Page column 27-28.
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 6103 - 6107.
[3]Patent: WO2008/129007,2008,A1 .Location in patent: Page/Page column 31-32.

5
[ 17159-79-4 ]
[ 2181-42-2 ]
[ 171361-65-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane; In acetonitrile; at 0 - 20℃; for 1.5h;Product distribution / selectivity;	Procedure 9b; A mixture of 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (1.14 ml, 3.94 mmol) and acetonitrile (15 ml) was added to a stirred suspension of trimethylsulphonium iodide (0.81 g, 3.97 mmol) and ethyl 4-oxocyclohexanecarboxylate (0.563 g, 3.31 mmol) at 0 0C. The mixture was stirred at 0 0C for 30 minutes then allowed to warm to room temperature and stirred for a further 1 hour. The reaction mixture was concentrated under reduced pressure then diluted with diethyl ether. The resulting suspension was stirred for 30 minutes then filtered and the filter cake was washed with more diethyl ether. The combined ethereal phases were concentrated under reduced pressure and the residue was chromatographed on SiO2 (Biotage 25M column) eluting with a gradient of 5%-15% EtOAc/cyclohexane to give a -60:40, trans:cis mixture of the title compound as a colourless oil (250 mg); <n="30"/>1 H NMR (400 MHz, CDCI3): delta 4.16 (2H both isomers, q), 2.65 (2H trans isomer, s), 2.62 (2H cis isomer, s), 2.35-2.48 (1 H both isomers, m), 1.68-2.14 (6H both isomers, m), 1.37- 1.52 (2H both isomers, m), 1.27 (3H both isomers, t).

References: [1]Patent: WO2008/92887,2008,A1 .Location in patent: Page/Page column 28-29.

6
[ 17159-79-4 ]
[ 1774-47-6 ]
[ 171361-65-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium tert-butylate; In dimethyl sulfoxide; at 20℃;Product distribution / selectivity;	Intermediate 9; Ethyl 1 -oxaspiror2.51octane-6-carboxylate; Procedure 9a; To a mixture of trimethylsulfoxonium iodide and potassium tert-butoxide (as reported in Synthetic Communications, 33(12), 2135-2143; 3.9 g, 11.76 mmol) was added a solution of ethyl 4-oxocyclohexanecarboxylate (1 g, 5.87 mmol, Aldrich) in DMSO (20ml). The mixture was left to stir overnight at room temperature. The mixture was poured into water and extracted with diethyl ether; the organic phase was dried on Na2SO4, filtered and evaporated in vacuo to afford the title compound (704.5 mg, 65%), which was used without purification.Another batch of the same compound prepared using an analogous method showed the following NMR spectra:1H NMR (400 MHz, CDCI3): delta 4.06 (2H, q), 2.49-2.59 (2H, m), 2.26-2.28 (1 H, m), 1.63- 2.04 (6H, m), 1.27-1.49 (2H, m), 1.20 (3H, t) cis/trans 65:35
	With potassium tert-butylate; In dimethyl sulfoxide; at 20℃;Product distribution / selectivity;	Intermediate delta: Ethyl 1-oxaspiror2.5loctane-6-carboxylate; To a mixture of trimethylsulfoxonium iodide and potassium tert-butoxide (as reported in Synthetic Communications, 33(12), 2135-2143; 3.9 g, 11.76 mmol) was added a solution of ethyl 4-oxocyclohexanecarboxylate (1 g, 5.87 mmole, Aldrich) in DMSO (20 ml). The mixture was left to stir overnight at room temperature. The mixture was poured into water and extracted with diethyl ether; the organic phase was dried on Na2SO4, filtered and evaporated in vacuo to afford ethyl 1-oxaspiro[2.5]octane-6-carboxylate (704.5 mg, 65%), which was used without purification. Another batch of the same compound prepared using an analogous method gave 1 H-NMR (400 MHz, CDCI3): delta 1.20 (t, 3 H), 1.27-1.49 (m, 2 H), 1.63-2.04 (m, 6 H), 2.26-2.28 (m, 1 H), 2.49-2.59 (m, 2 H), 4.06 (q, 2 H).

References: [1]Patent: WO2008/92887,2008,A1 .Location in patent: Page/Page column 28.
[2]Patent: WO2008/129007,2008,A1 .Location in patent: Page/Page column 32.

7
[ 51-79-6 ]
[ 171361-65-2 ]
(cis)-ethyl 2-oxo-1-oxa-3-azaspiro[4.5]decane-8-carboxylate [ No CAS ]
(trans)-ethyl 2-oxo-1-oxa-3-azaspiro[4.5]decane-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In N,N-dimethyl-formamide; at 130℃; for 18h;	Intermediates 15 and 16; Ethyl trans-2-oxo-1-oxa-3-azaspiror4.5ldecane-8-carboxylate (Intermediate 15) and ethyl cis^-oxo-i-oxa-S-azaspiroK.deltaidecane-delta-carboxylate (Intermediate 16); <n="34"/>Potassium tert-butoxide (23.14 g, 206 mmol) was added portionwise to a stirred solution of ethyl carbamate (27.6 g, 309 mmol) in DMF (200ml) at room temperature. The resulting cloudy mixture was stirred for 1 hour then a solution of ethyl 1-oxaspiro[2.5]octane-6- carboxylate (prepared in an analogous manner to intermediate 9 procedure 9b) (19 g, 103 mmol) in DMF (50 ml) was added. The reaction mixture was heated to 13O0C overnight (-18 hours). Cool and dilute with saturated NaCI solution (20 ml) and extract with AcOEt (4 x 100 ml_). The combined organic layers were dried (Na2SO4), filtered and concentrated to a pale yellow oil. The residue was purified via Biotage (cyclohexane:AcOEt starting from 1 :1 to AcOEt pure; 65M column) to give Intermediate 15 (8.24g) and intermediate 16 (4.36g);Intermediate 151H-NMR (400 MHz, CDCI3): delta 5.39 (1 H, brs), 4.15 (2H, q), 3.37 (2H, s), 2.47 (1 H, sept),2.01-2.1 1 (2H, m), 1.80-1.95 (4H, m), 1.62-1.74 (2H, m), 1.27 (3H, t).Intermediate 16.1H-NMR (400 MHz, CDCI3): delta 5.27 (1 H, brs), 4.15 (2H, q), 3.32 (2H, s), 2.28-2.37 (1 H, m), 2.13 (2H, brd), 1.85-2.05 (4H, m), 1.53 (2H, td), 1.27 (3H, t).
		Intermediate 40: Ethyl 2-oxo-1-oxa-3-azaspiro[4.51decane-8-carboxylate; Ethyl carbamate (15.60 g, 175 mmol) was dissolved in DMPU (107 ml). After cooling to 0 0C potassium tert-butoxide (13.10 g, 1 17 mmol) was added in portions over 5 min. The cooling bath was removed and the reaction mixture was stirred for 1 hour at r.t.. Ethyl 1- oxaspiro[2.5]octane-6-carboxylate (Intermediate 8, prepared according to the third method above described, 10.75 g, 58.4 mmol) dissolved in DMPU (20 ml) was added and the mixture heated at 130 0C for 15 hours. The mixture was allowed to cool to r.t. and quenched with sat. aq. NH4CI (60 ml) while cooling by means of an ice-bath. The bath was removed and further sat. aq. NH4CI (300 ml) was added until a clear solution was obtained, which was diluted further with brine (300 ml). The aqueous solution was extracted with DCM (3x400 ml). The combined organics were dried (Na2SO4), filtered and the DCM evaporated under reduced pressure. The remaining DMPU was stripped off under reduced pressure (80 0C, 0.1 Torr) over 7 hours. The obtained solid was purified by silica gel chromatography eluting with DCMEtOAc: 8/2. 10 g of the title compound was collected (44.0 mmol, 75%) along with a second slightly impure batch of 2 g (8.36 mmol; 14.3%) of the title compound. 1 H-NMR (400 MHz, CDCI3): delta 5.07-5.22 (1 H, m), 4.15 (2H, q), 3.37 (0.6H, s), 3.32 (0.4H, s), 2.42-2.53 (0.4H, m), 2.26-2.39 (0.6H, m), 2.01-2.18 (2H, m), 1.79-2.01 (4H, m), 1.63-1.75 (0.6H, m), 1.46-1.58 (1.4H, m), 1.27 (3H, t) (6:4 mixture of cis and trans isomers).

References: [1]Patent: WO2008/92887,2008,A1 .Location in patent: Page/Page column 32-33.
[2]Patent: WO2008/129007,2008,A1 .Location in patent: Page/Page column 47.

8
[ 51-79-6 ]
[ 171361-65-2 ]
[ 1044269-93-3 ]
[ 1044269-95-5 ]

Yield	Reaction Conditions	Operation in experiment
		Potassium tert-butoxide (23.14 g, 206 mmol) was added portion-wise to a stirred solution of ethyl carbamate (27.6 g, 309 mmol) in DMF (200 ml) at room temperature. The resulting cloudy mixture was stirred for 1 hour then a solution of <strong>[171361-65-2]ethyl 1-oxaspiro[2.5]octane-6-carboxylate</strong> (Intermediate 1, 19 g, 103 mmol) in DMF (50 ml) was added. The reaction mixture was heated to 130 C. overnight (18 hours). The mixture was cooled and diluted with saturated NaCl solution (20 ml) and extracted with AcOEt (4×100 ml). The combined organic layers were dried (Na2SO4), filtered and concentrated to a pale yellow oil. The residue was purified via Biotage (cyclohexane: AcOEt starting from 1:1 to AcOEt pure; 65i column) to give Intermediate 2 (8.24 g) and intermediate 3 (4.36 g); Intermediate 21H NMR (400 MHz, CDCl3): delta 5.39 (1H, br s), 4.15 (2H, q), 3.37 (2H, s), 2.47 (1H, sept), 2.01-2.11 (2H, m), 1.80-1.95 (4H, m), 1.62-1.74 (2H, m), 1.27 (3H, t).Intermediate 3.1H NMR (400 MHz, CDCl3): delta 5.27 (1H, br s), 4.15 (2H, q), 3.32 (2H, s), 2.28-2.37 (1H, m), 2.13 (2H, br d), 1.85-2.05 (4H, m), 1.53 (2H, td), 1.27 (3H, t).
		In a 1 L four-necked round bottom flask, to an ice-bath cooled solution of ethyl carbamate (41.2 g, 462 mmol) in dry DMPU (190 ml) potassium tert-butoxide (34.6 g, 308 mmol) was added portion-wise over 15 mins. The cooling bath was removed and the mixture was stirred at r.t. for 45 min under nitrogen atmosphere. The solution became cloudy. Ethyl 1-oxaspiro[2.5]octane-6-carboxylate (prepared in a similar fashion to the preparation of Intermediate 1, 28.4 g, 154 mmol) was added by a syringe and the mixture was heated at 130 C. for 22 hours. The mixture was allowed to cool to r.t. and quenched at 0 C. with saturated aqueous NH4Cl (200 ml). The ice-bath was removed and further sat aq NH4Cl was added (1000 ml) followed by brine (600 ml) until clear solution. The aqueous solution was extracted with DCM (3×800 ml). The combined organic extracts were dried (Na2SO4), filtered and DCM evaporated under reduced pressure. The remaining DMPU was stripped off in speedvacuum system (80 C., 0.1 Torr) for 20 hours affording a yellowish solid as crude material (33 g). Purification by silica gel chromatography (75 L Biotage column) eluting with cyclohexaneEtOAcMeOH 6:3.5:0.5 afforded: ethyl (trans)-2-oxo-1-oxa-3-azaspiro[4.5]decane-8-carboxylate (Intermediate 2, 13.7 g, 54.3 mmol) 1H NMR_(400 MHz, CDCl3): delta 1.28 (t, 3H), 1.70 (dd, 2H), 1.78-2.00 (m, 4H), 2.01-2.14 (m, 2H), 2.34-2.56 (m, 1H), 3.38 (s, 2H), 4.16 (q, 2H), 5.35 (br s, 1H); UPLCMS: 0.51 min, 228 [M+H]+ and 455 [2M+H]+.and ethyl (cis)-2-oxo-1-oxa-3-azaspiro[4.5]decane-8-carboxylate (Intermediate 3, 15.g, 68.6 mmol) 1H NMR (400 MHz, CDCl3): delta 1.26 (t, 3H), 1.45-1.61 (m, 2H), 1.84-2.04 (m, 4H), 2.11 (d, 2H), 2.32 (s, 1H), 3.32 (s, 2H), 4.15 (q, 2H), 5.98 (br s, 1H); UPLCMS: 0.50 min, 455 [2M+H]+.

References: [1]Patent: US2009/203705,2009,A1 .Location in patent: Page/Page column 22-23.
[2]Patent: US2009/203705,2009,A1 .Location in patent: Page/Page column 23.
[3]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 6103 - 6107.

9
[ 171361-65-2 ]
C₁₀H₁₈O₅ [ No CAS ]

References: [1]Synlett,2013,vol. 24,p. 502 - 506.

10
[ 171361-65-2 ]
(1s,4s)-4-(ethoxycarbonyl)-1-fluorocyclohexane-1-carboxylic acid [ No CAS ]

References: [1]Patent: US2018/127368,2018,A1 .

11
[ 171361-65-2 ]
(1s,4s)-ethyl 4-fluoro-4-(hydroxymethyl)cyclohexane-1-carboxylate [ No CAS ]
(1r,4r)-ethyl 4-fluoro-4-(hydroxymethyl)cyclohexane-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With pyridine; hydrogen fluoride; In dichloromethane; at -78℃; for 4.5h;	(1 s,4s)-4-fluoro-4-(hydroxymethyl)cyclohexane-1-carboxylate Hydrogen fluoride (70% in pyridine; 5 mL, 5.43 mmol) was cooled to -78 C. in a polypropylene vial and treated with a solution of the mixture of ethyl (3r,6r)-1-oxaspiro[2.5]octane-6-carboxylate and ethyl (3s,6r)-1-oxaspiro[2.5]octane-6-carboxylate from Step A (1.0 g, 5.43 mmol) in DCM (5 mL). The mixture was stirred at -78 C. for 4.5 h, then was poured into ice-cold 2 M aqueous NH4OH (25 mL) and DCM (25 mL). The mixture was adjusted to pH 8 using concentrated aqueous NH4OH and extracted with DCM (2*50 mL). The combined organic phases were washed sequentially with 1 M aqueous HCl (50 mL) and brine (50 mL), dried and concentrated. The residue was purified by column chromatography on silica gel (24 g), eluting with EtOAc-hexanes (gradient from 0-30%), to give (1s,4s)-ethyl 4-fluoro-4-(hydroxymethyl)cyclohexanecarboxylate as a solid (390 mg, 35% yield). 1H NMR (400 MHz, CDCl3) delta 4.21-4.07 (m, 2H), 3.57 (dd, J=19.6, 5.7 Hz, 2H), 2.36-2.20 (m, 1H), 2.05 (dd, J=12.4, 9.4 Hz, 2H), 1.96-1.86 (m, 2H), 1.86-1.73 (m, 2H), 1.47-1.28 (m, 2H), 1.26 (t, J=7.2 Hz, 3H). (1s,4r)-ethyl 4-fluoro-4-(hydroxymethyl)cyclohexanecarboxylate was also isolated. 1H NMR (400 MHz, CDCl3) delta 4.14 (q, J=7.1 Hz, 2H), 3.72-3.55 (m, 2H), 2.62-2.46 (m, 1H), 1.99-1.87 (m, 2H), 1.85-1.72 (m, 6H), 1.26 (t, J=7.2 Hz, 3H).

References: [1]Patent: US2018/127368,2018,A1 .Location in patent: Paragraph 0453-0454.

12
[ 22013-33-8 ]
[ 171361-65-2 ]
trans-3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2-oxo-1-oxa-3-azaspiro[4.5]decane-8-carboxylic acid ethyl ester [ No CAS ]

References: [1]Patent: WO2008/26172,2008,A1 .

13
[ 171361-65-2 ]
(trans)-2-oxo-3-(2-pyridinyl)-1-oxa-3-azaspiro[4.5]decane-8-carboxylic acid [ No CAS ]