15963-40-3|Methyl 3-methylenecyclobutanecarboxylate| Ambeed

CAS No. :	15963-40-3
Formula :	C₇H₁₀O₂
M.W :	126.15
SMILES Code :	COC(=O)C1CC(=C)C1
MDL No. :	MFCD01087180
InChI Key :	OSWTXCSCDKIANQ-UHFFFAOYSA-N
Pubchem ID :	11051654

Safety of [ 15963-40-3 ]

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

Application In Synthesis of [ 15963-40-3 ]

* 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 [ 15963-40-3 ]

[ 15963-40-3 ] Synthesis Path-Downstream 1~55

1
[ 463-49-0 ]
[ 292638-85-8 ]
[ 15963-40-3 ]

References: [1]Journal of the American Chemical Society,1959,vol. 81,p. 2723,2725.

2
[ 186581-53-3 ]
[ 15760-35-7 ]
[ 15963-40-3 ]

References: [1]Journal of the American Chemical Society,1970,vol. 92,p. 3688 - 3696.

3
[ 186581-53-3 ]
[ 10555-42-7 ]
[ 15963-40-3 ]

References: [1]Chemische Berichte,1967,vol. 100,p. 3614 - 3624.

4
[ 186581-53-3 ]
[ 15760-36-8 ]
[ 15963-40-3 ]

References: [1]Chemische Berichte,1967,vol. 100,p. 2107 - 2116.

5
[ 67-56-1 ]
[ 15963-40-3 ]
[ 5119-74-4 ]

References: [1]Tetrahedron,1965,vol. 21,p. 2749 - 2769.

6
[ 917-64-6 ]
[ 15963-40-3 ]
[ 29555-06-4 ]

References: [1]Journal of the American Chemical Society,1970,vol. 92,p. 3688 - 3696.

7
[ 15963-40-3 ]
[ 14924-54-0 ]

References: [1]Journal of Organic Chemistry,1967,vol. 32,p. 3950 - 3955.

8
[ 15963-40-3 ]
[ 10555-45-0 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

9
[ 15963-40-3 ]
[ 89892-95-5 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

10
[ 15963-40-3 ]
[ 695-95-4 ]

References: [1]Chemische Berichte,1967,vol. 100,p. 2107 - 2116.

11
[ 89892-95-5 ]
[ 30493-92-6 ]
[ 15963-40-3 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 777 - 778.
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 870.

12
[ 89892-95-5 ]
[ 15963-40-3 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 777 - 778.
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 870.

13
[ 15963-40-3 ]
1-Oxa-spiro[2.3]hexane-5-carboxylic acid methyl ester [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,1995,vol. 31,p. 1142.
Zhurnal Organicheskoi Khimii,1995,vol. 31,p. 1251.

16
[ 67-56-1 ]
[ 15963-40-3 ]
methyl trans-3-bromomethyl-3-methoxycyclobutane-1-carboxylate [ No CAS ]
methyl cis-3-bromomethyl-3-methoxycyclobutane-1-carboxylate [ No CAS ]
methyl cis-3-bromo-3-methoxymethylcyclobutane-1-carboxylate [ No CAS ]
methyl trans-3-bromo-3-methoxymethylcyclobutane-1-carboxylate [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 40 - 48.

17
[ 15963-40-3 ]
[ 578715-80-7 ]
[ 578715-81-8 ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.

18
[ 15963-40-3 ]
methyl cis-3-bromo-3-bromomethylcyclobutane-1-carboxylate [ No CAS ]
methyl trans-3-bromo-3-bromomethylcyclobutane-1-carboxylate [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 40 - 48.

19
[ 15963-40-3 ]
[ 578715-77-2 ]
[ 578715-76-1 ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.

20
[ 15963-40-3 ]
ethyl nitrodiazoacetic ester [ No CAS ]
1-nitro-spiro[2.3]hexane-1,5-dicarboxylic acid 1-ethyl ester 5-methyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 8241 - 8244.

21
[ 15963-40-3 ]
1-amino-spiro[2.3]hexane-1,5-dicarboxylic acid [ No CAS ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 8241 - 8244.

22
[ 15963-40-3 ]
methyl 3-hydroxymethylbicyclo[1.1.0]butane-1-carboxylate [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.
[2]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.
[3]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.
[4]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.
[5]Russian Journal of Organic Chemistry,1995,vol. 31,p. 1142.
Zhurnal Organicheskoi Khimii,1995,vol. 31,p. 1251.

23
[ 15963-40-3 ]
methyl 3-bromomethylenecyclobutane-1-carboxylate [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 40 - 48.
[2]Russian Journal of Organic Chemistry,2003,vol. 39,p. 40 - 48.

24
[ 15963-40-3 ]
methyl 3-bromomethylbicyclobutane-1-carboxylate [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 40 - 48.
[2]Russian Journal of Organic Chemistry,2003,vol. 39,p. 40 - 48.

25
[ 15963-40-3 ]
[ 578715-80-7 ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.

26
[ 15963-40-3 ]
[ 578715-81-8 ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.

27
[ 15963-40-3 ]
N,N-diisopropyl-3-hydroxymethylbicyclobutane-1-carboxamide [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.
[2]Russian Journal of Organic Chemistry,2003,vol. 39,p. 33 - 39.

28
[ 15963-40-3 ]
[ 89580-49-4 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

29
[ 15963-40-3 ]
[ 10555-43-8 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

30
[ 15963-40-3 ]
[ 311-75-1 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

31
[ 15963-40-3 ]
(3-methylenecyclobutyl)methyl-4-methylbenzenesulfonate [ No CAS ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

32
[ 15963-40-3 ]
[ 10555-46-1 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

33
[ 15963-40-3 ]
[ 10555-48-3 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

34
[ 15963-40-3 ]
[ 10555-42-7 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 4437 - 4441.

35
[ 15760-35-7 ]
[ 15963-40-3 ]

References: [1]Chemische Berichte,1967,vol. 100,p. 2107 - 2116.
[2]Patent: WO2012/154204,2012,A1 .
[3]Patent: WO2015/66413,2015,A1 .
[4]Patent: WO2015/129926,2015,A1 .
[5]Patent: WO2015/180612,2015,A1 .
[6]Patent: WO2015/196071,A1 .
Patent: ,2015, .
[7]Patent: WO2016/105468,2016,A1 .
[8]Patent: CN105566324,2016,A .
[9]Patent: WO2016/115090,2016,A1 .
[10]Patent: WO2017/40606,2017,A1 .
[11]Patent: WO2018/69863,2018,A1 .
[12]Patent: WO2018/229629,2018,A1 .
[13]Patent: WO2019/63748,2019,A1 .

36
[ 408326-43-2 ]
[ 15963-40-3 ]

References: [1]Chemische Berichte,1967,vol. 100,p. 3614 - 3624.

37
[ 5164-23-8 ]
[ 15963-40-3 ]

References: [1]Chemische Berichte,1967,vol. 100,p. 3614 - 3624.

38
[ 5164-22-7 ]
[ 15963-40-3 ]

References: [1]Chemische Berichte,1967,vol. 100,p. 3614 - 3624.

39
diethyl[nitro(diazo)methyl]phosphonate [ No CAS ]
[ 15963-40-3 ]
[ 1219792-02-5 ]

References: [1]Synthesis,2010,p. 259 - 266.

40
[ 75-11-6 ]
[ 15963-40-3 ]
[ 1383823-60-6 ]

Yield	Reaction Conditions	Operation in experiment
72%		To a solution of Et2Zn (11.89 mL, 11.89 mmol) in DCM (10 mL) was added a solution of TFA (0.88 mL, 11.89 mmol) in DCM (10 mL) dropwise at 0 C for 30 minutes. A solution of CH2I2 (0.96 mL, 11.89 mmol) in DCM (10 mL) was added dropwise at 0 C for 45 minutes. The reaction mixture was stirred at 0 C for 1 hour. A solution of methyl 3- methylenecyclobutanecarboxylate (500 mg, 3.96 mmol) in DCM (5 mL) was added to the reaction mixture. The reaction mixture was allowed to warm to 15 C for 16 hours. Saturated NH4CI solution (50 mL) was added to the reaction mixture and the mixture was extracted with DCM (50 mL c 2). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated. The crude residue was purified by silica gel column chromatography (10 % EtOAc in petroleum ether) to afford the title compound (400 mg, 72 %) as a yellow oil. ' H NMR (400 MHz, CDCl3) d 3.71 (s, 3H), 3.34 - 3.27 (m, 1H), 2.53 - 2.48 (m, 2H), 2.26 - 2.20 (m, 2H), 0.49 - 0.42 (m, 4H).
63%		To a solution of diethylzinc (1.0 M in hexane, 46 mL, 46 mmol) in DCM (200 mL) was added a solution of TFA (3.54 mL, 46 mmol) in DCM (50 mL) dropwise at 0 C for 30 min. A solution of diiodomethane (3.7 mL, 46 mmol) in DCM (50 mL) was added dropwise at 0 C for 45 min. The mixture was stirred at the same temperature for 1 h. A solution of compound A141-2 (2.52 g, 20 mmol) in DCM (30 mL) was added to the reaction mixture. The mixture was allowed to warm to room temperature for overnight. The reaction mixture was quenched with saturated NH4C1 aq. (200 mL) and extracted with DCM. The collected organic layer was dried over MgS04 and concentrated under reduced pressure. The residue was purified by silicagel chromatography (20% EtOAc/hexane as eluent) to provide compound Al 41-3 (1.77 g, 63%) as a colorless oil.
		A cold (0C) solution of diethyl zinc (79.3 mL, 1.0 M in Hexanes) in dichloromethane (66 mL) was treated with the dropwise addition of TFA (6.11 mL, 79.3 mL) in dichloromethane (27 mL). After 1 hour of stirring, diiodomethane (6.39 mL, 79.3 mmol) in dichloromethane (27 mL) was then introduced. After 40 min, I-13A (4.00 g, 31.7 mmol) dichloromethane (10 mL) was added dropwise. The reaction was left to stir for 2 hours and then quenched with sat'd NH4CI (aq.). Phases were separated and the organic phase collected, dried (MgS04), filtered, concentrated, and distilled (42-44C, 0.1 mmHg) to afford the desired spirocycle. (400 MHz, CDC13) delta 3.69 (s, 3H), 3.28 (m, 1H), 2.49 (m, 2H), 2.22 (m, 2H), 0.43 (m, 4H); MS m/z 141.1 (M + 1).

1.9 g

Description 67Methyl spiroL2.3]hexane-5-carboxylate (D67)To an ice-cooled (0C) solution of diethylzinc (1.0 M in hexane) (39.6 mL) in DCM (30 mL) was added dropwise a solution of TFA (3.05 mL) in DCM (10 mL). After one hour of stirring, diiodomethane (10.62 g) in DCM (10 mL) was then introduced. After 40 mm, the solution of methyl 3-methylene cyclobutanecarboxylate (D66, 2.0 g) in DCM (4 mL) was added dropwise. Thereaction was stirred at RT for 2 hours and then quenched with saturated NH4C1 solution (30 mL).The organic layer was separated, dried and concentrated to afford the title compound (1.9 g) as paleyellow oil. MS (ESI): C8H1202 requires 140; found 139 [M-H].

References: [1]Patent: WO2020/51099,2020,A1 .Location in patent: Paragraph 0660-0663.
[2]Patent: WO2015/129926,2015,A1 .Location in patent: Page/Page column 109.
[3]Patent: WO2012/87519,2012,A1 .Location in patent: Page/Page column 104.
[4]Patent: WO2015/180612,2015,A1 .Location in patent: Page/Page column 60.

41
[ 67-56-1 ]
[ 15760-36-8 ]
[ 15963-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	With diazomethyl-trimethyl-silane; In hexanes; dichloromethane; at 0℃; for 0.5h;	A cold (0C) solution of 3- methylenecyclobutanecarboxylic acid (WO2007/063391, 6.07 g, 54.1 mmol) indichloromethane (180 mL) and methanol (18 mL) was treated with the dropwise addition of (trimethylsilyl)diazomethane (28.4 mL, 2.0 M in Hexanes). After 30 min, 1 mL of cone. HOAc was added and the reaction concentrated in vacuo. (400 MHz, CDC13) delta 4.78 (m, 2H), 3.67 (s, 3H), 3.10 (m, 1H), 2.98 (m, 2H), 2.88 (m, 2H); MS m/z 127.1 (M + 1).

References: [1]Patent: WO2012/87519,2012,A1 .Location in patent: Page/Page column 104.

42
[ 15963-40-3 ]
[ 1383823-62-8 ]

References: [1]Patent: WO2012/87519,2012,A1 .

43
[ 15963-40-3 ]
[ 1383823-64-0 ]

References: [1]Patent: WO2012/87519,2012,A1 .

44
[ 15963-40-3 ]
spiro[2.3]hexane-5-carbaldehyde [ No CAS ]

References: [1]Patent: WO2015/129926,2015,A1 .
[2]Patent: WO2012/87519,2012,A1 .

45
[ 15963-40-3 ]
[ 1383823-66-2 ]

References: [1]Patent: WO2012/87519,2012,A1 .

46
[ 15760-36-8 ]
[ 77-78-1 ]
[ 15963-40-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate; In acetone; at 25 - 70℃; for 12h;	The methylene-cyclobutane carboxylic acid (11.0g, 98.1mmol) and potassium carbonate (27.1g, 196mmol) was dissolved in acetone (100 mL) was added at 25C dimethyl sulfate (14.8g, 117mmol), 70C after 12 hours. Was added water (20 mL) to quench the reaction, and extracted with dichloromethane (30mLx3), dried over anhydrous sulfateSodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give methyl-3-methylenecyclobutanoate (12.0 g of, yellow oil),Yield: 97%.
91%	With potassium carbonate; In acetone; for 2h;Reflux;	The mixture of 3-methylenecyclobutanecarboxylic acid (6.0g, 53.5 mmol), K2CO3 (14.79 g, 107 mmol) and Me2S04 (7.67 mL, 80 mmol) in Acetone (100 mL) was heated to reflux for 2h. The reaction mixture was cooled to room temperature and filtered. The solvent was removed under reduced pressure. The residue was purified with silica gel chromatography (hexane/EtOAc = 20/1 ) to afford the desired product methyl 3- methylenecyclobutanecarboxylate (6.8 g, 48.5 mmol, 91 % yield) as colorless oil. m/z: [M + H]+ Calcd for C6H802 1 13.1 ; Found 1 13.2.
88%	With potassium carbonate; In acetone; at 100℃; for 2h;	3.1 .57a (24.2 g, 216 mmol, 1.0 equiv) was dissolved in acetone (100 mL). K2C03 (59.6 g, 432.1 mmol, 2.0 equiv), Me2SO4 (32.7 g, 259.2 mmol, 1.2 equiv) was added and the reaction mixture was stirred at 100 C for 2 hours. The reaction mixture was filtered and filtrate was concentrated to afford a crude residue which was purified by silica gel chromatography (100 % n-pentane) to afford product 3.1.57b (24 g, 88 % yield). 1H NMR (400 MHz, DMSO) 64.82-4.77 (m, 2H), 3.62 (s, 3H), 3.22-3.12 (m, 1H), 2.91 -2.83(m, 4H).

84%	With potassium carbonate; In acetone; for 2h;Reflux;	The mixture of 3-methylenecyclobutanecarboxylic acid 2 (29.12g, 0.26mol), potassium carbonate (70.2g, 0.52mol), acetone (500ml_) and dimethyl sulfate (39.312g, 0.312mol) was heated to reflux for 2h. The reaction mixture was cooled to room temperature and filtered. The solvent was removed under reduced pressure. The residue was purified with silica gel chromatography to afford the desired product as colorless oil. (27.5g, yield=84%).
2.1 g	With potassium carbonate; In acetone; for 2h;Reflux;	Description 663-Methylenecyclobutanecarboxylate (D66)LfThe mixture of 3-methylenecyclobutanecarboxylic acid (D65, 6.0 g), K2C03 (14.79 g) and Me2SO4 (7.67 mL) in acetone (100 mL) was heated to reflux for 2 hours. The reaction mixture was cooled to RT and filtered. The solvent was removed under reduced pressure, and the residue was purifiedwith column chromatography (silica gel, petroleum ether/EtOAc = 20:1) to afford the title compound (2.1 g) as colorless oil. ?H NIVIR (500 MHz, DMSO-d6): 4.80-4.75 (m, 2H), 3.62 (s, 3H), 3.20-3.12 (m, lH), 2.89-2.81 (m, 4H).
	With potassium carbonate; In acetone; at 60℃; for 2h;	potassium carbonate (61.5 g, 444.98 mmol, 2.00 eq.) and dimethyl sulfate (33 g, 261.63 mmol, 1.20 eq.) were added to a solution of 3-methylidenecyclobutane-1-carboxylic acid (25 g, 222.96 mmol, 1.00 eq.) in acetone (300 mL). The resulting solution was stirred for 2 hours at 60 C. The resulting solution was diluted with water (700 mL) and then extracted with ethyl acetate (2x500 mL) andthe organic layers combined. The resulting mixture was washed with brine (2x500 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 30 g (crude) of methyl 3-methylidenecyclobutane-1-carboxylate as yellow oil.
	With potassium carbonate; In acetone; at 60℃; for 2h;	Step lb: methyl 3-methylenecyclobutane-l-carboxylate: potassium carbonate (61.5 g, 444.98 mmol, 2.00 eq.) and dimethyl sulfate (33 g, 261.63 mmol, 1.20 eq.) were added to a solution of 3-methylidenecyclobutane-l-carboxylic acid (25 g, 222.96 mmol, 1.00 eq.) in acetone (300 mL). The resulting solution was stirred for 2 hours at 60 C. The resulting solution was diluted with water (700 mL) and then extracted with ethyl acetate (2x500 mL) and the organic layers combined. The resulting mixture was washed with brine (2x500 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 30 g (crude) of methyl 3-methylidenecyclobutane-l -carboxylate as yellow oil.
	With potassium carbonate; In acetone; at 60℃; for 2h;	potassium carbonate (61.5 g, 444.98 mmol, 2.00 eq.) and dimethyl sulfate (33 g, 261.63 mmol, 1.20 eq.) were added to a solution of 3-methylidenecyclobutane-l-carboxylic acid (25 g, 222.96 mmol, 1.00 eq.) in acetone (300 mL). The resulting solution was stirred for 2 hours at 60 C. The resulting solution was diluted with water (700 mL) and then extracted with ethyl acetate (2x500 mL) and the organic layers combined. The resulting mixture was washed with brine (2x500 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 30 g (crude) of methyl 3-methylidenecyclobutane-l-carboxylate as yellow oil.
	With potassium carbonate; In acetone; at 60℃; for 2h;	potassium carbonate (61.5 g, 444.98 mmol, 2.00 eq.) and dimethyl sulfate (33 g, 261.63 mmol, 1.20 eq.) were added to a solution of 3-methylidenecyclobutane-l-carboxylic acid (25 g, 222.96 mmol, 1.00 eq.) in acetone (300 mL). The resulting solution was stirred for 2 hours at 60 C. The resulting solution was diluted with water (700 mL) and then extracted with ethyl acetate (2x500 mL) and the organic layers combined. The resulting mixture was washed with brine (2x500 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 30 g (crude) of methyl 3-methylidenecyclobutane-l-carboxylate as yellow oil.

References: [1]Patent: CN105566324,2016,A .Location in patent: Paragraph 0197; 0201; 0202; 0203.
[2]Patent: WO2019/63748,2019,A1 .Location in patent: Page/Page column 234.
[3]Patent: WO2015/66413,2015,A1 .Location in patent: Page/Page column 131.
[4]Patent: WO2012/154204,2012,A1 .Location in patent: Page/Page column 67; 68.
[5]Patent: WO2015/180612,2015,A1 .Location in patent: Page/Page column 60.
[6]Patent: WO2015/196071,A1 .Location in patent: Paragraph 0174.
Patent: ,2015, .Location in patent: Paragraph 0174.
[7]Patent: WO2016/105468,2016,A1 .Location in patent: Paragraph 0136.
[8]Patent: WO2016/115090,2016,A1 .Location in patent: Paragraph 0171.
[9]Patent: WO2017/40606,2017,A1 .Location in patent: Paragraph 0130.

47
[ 15963-40-3 ]
[ 89941-55-9 ]

Yield	Reaction Conditions	Operation in experiment
95%		A dry three-neck flask was charged with methyl 3- methylenecyclobutanecarboxylate 3 (24.46g, 0.21 mol) and dry THF (130ml) and cooled to -10C, then borane-THF complex (70.0mL) was added via a syringe dropwise. The resulting mixture was stirred for 4h at r.t and was cooled to -20C~- 10C; methanol was added, stirred for 15min. Sodium hydroxide (3M 30ml_) and hydrogen peroxide (34. Og, 0.21 Omol) were added in sequence. The mixture was stirred for 2h and saturated sodium sulfite solution (100ml_) was added. The reaction mixture was diluted with water, then extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, removed the solvent and the residue was purified with silica gel chromatography. (28.73g, 95%)
87%		Methyl-3-methylene cyclobutane carboxylic acid(2.00g, 15.8mmol) was dissolved in tetrahydrofuran (30 mL), andWas added dropwise at -10C borane dimethyl sulfide (3.61g, 47.5mmol), then -10C for 3 hours, was added 3N aqueous sodium hydroxide (10mL) and hydrogen peroxide (5mL), reaction was continued for 1 hour, the reaction solution was added a saturated aqueous sodium thiosulfate solution (30 mL) to quench the reaction, and extracted with dichloromethane (10mLx3), dried over anhydrous Sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give methyl 3-(hydroxymethyl)cyclobutanoate (2.00 g,Yellow oil). Yield: 87%.
68%		3.1.57b (24 g, 190.4 mmol, 1.0 equiv) was dissolved in THE and cooled to -15 C. BH3.Me2S (14.4 g, 190.4 mmol, 1.0 equiv) was added drop wise and the reaction mixture was stirred at room temperature for 4 hours. Cooled the reaction mixture at -15 C, NaOH (3M) (25 mL), H202 (50%) (12.9 g, 190.4 mmol, 1.0 equiv) were added and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with sodium bisulphate and extracted with EtOAc. The organic layer was washed with brine,dried over sodium sulfate and concentrated to afford a crude residue. The crude residue was purified by silica gel column chromatography (70 % EtOAc in Hexane) to afford product 3.1.57c (18.7 g, 68 % yield). 1H NMR (400 MHz, DMSO) 64.54 (d, J = 29.8 Hz, 1H), 3.62-3.55 (m, 3H), 3.41 (d, J = 6.5 Hz, 1H), 3.30 (d, J = 6.0 Hz, 1H), 3.13-2.95 (m, 1H), 2.37-2.27 (m, 1H), 2.15 (ddt, J= 8.7, 7.8, 6.2 Hz, 2H), 1.98- 1.84(m, 2H).

58%		a solution of borane-THF (56 mL, 0.80 eq.) was added dropwise over 30 mm to a cold (-10 C) solution of <strong>[15963-40-3]methyl 3-methylidenecyclobutane-1-carboxylate</strong> (10 g, 79.27 mmol, 1.00 eq.) in THF (100 mL). The resulting solution was stirred for 3 hours at 25 C. The mixture was cooled to -10 Cand methanol (20 mL) was added slowly and the mixture was stirred for 30 mm at 25 C. The reaction mixture was cooled to -10 C and H202 (9 g, 79.41 mmol, 1.00 eq., 30%) was added dropwise (5 mm) followed by dropwise addition of sodium hydroxide aqueous (12.5 mL) at -10C. The resulting solution was stirred for 3 hours at 25 C. The reaction was then quenched by the addition of Na2SO3 aqueous. The resulting solution was diluted with water (300 mL) andthen extracted with ethyl acetate (2x300 mL) and the organic layers combined. The resulting mixture was washed with brine (2x300 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give methyl 3 -(hydroxymethyl)cyclobutane- 1 -carboxylate as colorless oil (6.6 g, 58%).
54%		To a solution of <strong>[15963-40-3]methyl <strong>[15963-40-3]3-methylenecyclobutanecarboxylate</strong></strong> (5.3 g, 42.4 mmol, 1.0 eq) in THF (30 mL) was added BH3 (12.6 mL, 12.6 mmol, 0.3 eq, 1 M) dropwise at 0 C. Then the reaction mixture was warmed to ft and stirred for 4 h. MeOH (15 mL) was added and the mixture was stirred for 30 mm at 0 C. NaOH (4.2 mL, 3M) and H202 (1.4 g, 42.4 mmol, 1.0 eq) wereadded and stirred at 0 C for 1 h. The mixture was quenched with water (30 mL) and extracted with Et20 (60 mL X 2). The combined organic phases were dried over Na2SO4 After filtration and concentration, 3.3 g of methyl 3-(hydroxymethyl)cyclobutanecarboxylate as yellow oil was obtained. Y: 54%. ESI-MS (M+H): 145.0. ?H NMR (400 MHz, CD3OD) (5: 3.69 (s, 1.3H), 3.67 (s, 1.7H), 3.59 (s, 0.4H), 3.58 (s, 0.5H), 3.50 (s, 0.4H), 3.48 (s, 0.5H), 3.12-3.03 (m, 1H), 2.48-2.38 (m, 1H), 2.35-2.22 (m, 2H), 2.08-1.94 (m, 2H).
2.92%		A dry three-neck flask was charged with <strong>[15963-40-3]methyl <strong>[15963-40-3]3-methylenecyclobutanecarboxylate</strong></strong> (6 g, 47.6 mmol) and dry THF (20 ml) and cooled to -10 C. BH3.THF (12.26 g, 143 mmol) was then added via a syringe dropwise. The resulting mixture was stirred for 4h at rt and was cooled to -20 C - 10C. Methanol was then added and the mixture was stirred for 15min. Sodium hydroxide (3M; 30 ml) and H2O2 (7.29 ml_, 238 mmol) were added in sequence. The mixture was stirred for 2h and a saturated sodium sulfite solution (100 ml) was added. The reaction mixture was diluted with water, then extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, and the residue was purified by flash chromatography eluting with (petroleum ether/EtOAc = 3/1 ) to afford methyl 3- (hydroxymethyl)cyclobutanecarboxylate (250 mg, 1 .387 mmol, 2.92 % yield) as a yellow oil.
6.6 g		Step 1C: methyl 3-(hydroxymethyl)cyclobutane-l-carboxylate: a solution of borane-THF (56 mL, 0.80 eq.) was added dropwise over 30 min to a cold (-10 C) solution of methyl 3-methylidenecyclobutane-l -carboxylate (10 g, 79.27 mmol, 1.00 eq.) in THF (100 mL). The resulting solution was stirred for 3 hours at 25 C. The mixture was cooled to -10 C and methanol (20 mL) was added slowly and the mixture was stirred for 30 min at 25 C. The reaction mixture was cooled to -10 C and H202 (9 g, 79.41 mmol, 1.00 eq., 30%) was added dropwise (5 min) followed by dropwise addition of sodium hydroxide aqueous (12.5 mL) at -10 C. The resulting solution was stirred for 3 hours at 25 C. The reaction was then quenched by the addition of Na2S03 aqueous. The resulting solution was diluted with water (300 mL) and then extracted with ethyl acetate (2x300 mL) and the organic layers combined. The resulting mixture was washed with brine (2x300 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give methyl 3-(hydroxymethyl)cyclobutane- l -carboxylate as colorless oil (6.6 g, 58%).
6.6 g		a solution of borane-THF (56 mL, 0.80 eq.) was added dropwise over 30 min to a cold (-10 C) solution of methyl 3-methylidenecyclobutane-l-carboxylate (10 g, 79.27 mmol, 1.00 eq.) in THF (100 mL). The resulting solution was stirred for 3 hours at 25 C. The mixture was cooled to -10 C and methanol (20 mL) was added slowly and the mixture was stirred for 30 min at 25 C. The reaction mixture was cooled to -10 C and H2O2 (9 g, 79.41 mmol, 1.00 eq., 30%) was added dropwise (5 min) followed by dropwise addition of sodium hydroxide aqueous (12.5 mL) at -10 C. The resulting solution was stirred for 3 hours at 25 C. The reaction was then quenched by the addition of Na2SC>3 aqueous. The resulting solution was diluted with water (300 mL) and then extracted with ethyl acetate (2x300 mL) and the organic layers combined. The resulting mixture was washed with brine (2x300 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give methyl 3-(hydroxymethyl)cyclobutane-l-carboxylate as colorless oil ( 6.6 g, 58%).
6.6 g		a solution of borane-THF (56 mL, 0.80 eq.) was added dropwise over 30 min to a cold (-10 C) solution of methyl 3-methylidenecyclobutane-l -carboxylate (10 g, 79.27 mmol, 1.00 eq.) in THF (100 mL). The resulting solution was stirred for 3 hours at 25 C. The mixture was cooled to -10 C and methanol (20 mL) was added slowly and the mixture was stirred for 30 min at 25 C. The reaction mixture was cooled to -10 C and H2O2 (9 g, 79.41 mmol, 1.00 eq., 30%) was added dropwise (5 min) followed by dropwise addition of sodium hydroxide aqueous (12.5 mL) at -10 C. The resulting solution was stirred for 3 hours at 25 C. The reaction was then quenched by the addition of Na2SC>3 aqueous. The resulting solution was diluted with water (300 mL) and then extracted with ethyl acetate (2x300 mL) and the organic layers combined. The resulting mixture was washed with brine (2x300 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give methyl 3-(hydroxymethyl)cyclobutane-l -carboxylate as colorless oil ( 6.6 g, 58%).

References: [1]Patent: WO2012/154204,2012,A1 .Location in patent: Page/Page column 67; 68; 69.
[2]Patent: CN105566324,2016,A .Location in patent: Paragraph 0197; 0204; 0205; 0206.
[3]Patent: WO2015/66413,2015,A1 .Location in patent: Page/Page column 131; 132.
[4]Patent: WO2019/201283,2019,A1 .Location in patent: Page/Page column 137; 138.
[5]Patent: WO2015/196071,A1 .Location in patent: Paragraph 0175.
Patent: ,2015, .Location in patent: Paragraph 0175.
[6]Patent: WO2017/127430,2017,A1 .Location in patent: Page/Page column 25; 26.
[7]Patent: WO2019/63748,2019,A1 .Location in patent: Page/Page column 234-235.
[8]Patent: WO2016/105468,2016,A1 .Location in patent: Paragraph 0137.
[9]Patent: WO2016/115090,2016,A1 .Location in patent: Paragraph 0172.
[10]Patent: WO2017/40606,2017,A1 .Location in patent: Paragraph 0131.

48
[ 15963-40-3 ]
(trans)-methyl 3-formylcyclobutanecarboxylate [ No CAS ]

References: [1]Patent: WO2012/154204,2012,A1 .

49
[ 15963-40-3 ]
(cis)-methyl 3-formylcyclobutanecarboxylate [ No CAS ]

References: [1]Patent: WO2012/154204,2012,A1 .

50
[ 15963-40-3 ]
(cis)-methyl 3-(2,2-dibromovinyl)cyclobutanecarboxylate [ No CAS ]

References: [1]Patent: WO2012/154204,2012,A1 .

51
[ 15963-40-3 ]
((cis)-3-(2,2-dibromovinyl)cyclobutyl)methanol [ No CAS ]

References: [1]Patent: WO2012/154204,2012,A1 .

52
[ 15963-40-3 ]
methyl 4-(((cis)-3-(hydroxymethyl)cyclobutyl)buta-1,3-diynyl)benzoate [ No CAS ]

References: [1]Patent: WO2012/154204,2012,A1 .

53
[ 15963-40-3 ]
4-(((cis)-3-(hydroxymethyl)cyclobutyl)buta-1,3-diynyl)benzoic acid [ No CAS ]

References: [1]Patent: WO2012/154204,2012,A1 .

54
[ 15963-40-3 ]
(trans)-methyl 3-(2,2-dibromovinyl)cyclobutanecarboxylate [ No CAS ]

References: [1]Patent: WO2012/154204,2012,A1 .

55
[ 15963-40-3 ]
((trans)-3-(2,2-dibromovinyl)cyclobutyl)methanol [ No CAS ]

References: [1]Patent: WO2012/154204,2012,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Halogenation • Heat of Combustion • Reactions of Amines • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

Related Functional Groups of
[ 15963-40-3 ]

Alkenyls

A161969 [145576-28-9]

Ethyl 4-methylenecyclohexanecarboxylate

Similarity: 0.88

A123538 [32853-30-8]

Methyl 5-methylhex-5-enoate

Similarity: 0.84

A285859 [56124-48-2]

6-(Methoxycarbonyl)cyclohex-3-enecarboxylic acid

Similarity: 0.82

A363588 [58101-60-3]

Methyl 3-cyclopentenecarboxylate

Similarity: 0.82

A163285 [40637-56-7]

Dimethyl 2-allylmalonate

Similarity: 0.79

Aliphatic Cyclic Hydrocarbons

A161969 [145576-28-9]

Ethyl 4-methylenecyclohexanecarboxylate

Similarity: 0.88

A285859 [56124-48-2]

6-(Methoxycarbonyl)cyclohex-3-enecarboxylic acid

Similarity: 0.82

A363588 [58101-60-3]

Methyl 3-cyclopentenecarboxylate

Similarity: 0.82

A387227 [83249-10-9]

3-(Methoxycarbonyl)bicyclo[1.1.1]pentane-1-carboxylic acid

Similarity: 0.81

A500140 [115913-32-1]

Dimethyl bicyclo[1.1.1]pentane-1,3-dicarboxylate

Similarity: 0.81

Esters

A161969 [145576-28-9]

Ethyl 4-methylenecyclohexanecarboxylate

Similarity: 0.88

A123538 [32853-30-8]

Methyl 5-methylhex-5-enoate

Similarity: 0.84

A285859 [56124-48-2]

6-(Methoxycarbonyl)cyclohex-3-enecarboxylic acid

Similarity: 0.82

A363588 [58101-60-3]

Methyl 3-cyclopentenecarboxylate

Similarity: 0.82

A500140 [115913-32-1]

Dimethyl bicyclo[1.1.1]pentane-1,3-dicarboxylate

Similarity: 0.81

Precautionary Statements-General
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P378
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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.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
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Storage
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P401
P402	Store in a dry place.
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P411
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P413
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Disposal
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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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
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
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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Health hazards
Code	Phrase
H300	Fatal if swallowed
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H302	Harmful if swallowed
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
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H314	Causes severe skin burns and eye damage
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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
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

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CAS No.: 15963-40-3

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CAS No.: 15963-40-3

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[ 15963-40-3 ] Synthesis Path-Downstream 1~55

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[ 15963-40-3 ]

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{[proInfo.proName]}

CAS No.: 15963-40-3

{[proInfo.proName]}

CAS No.: 15963-40-3

Alternative Products

Product Details of [ 15963-40-3 ]

Safety of [ 15963-40-3 ]

Application In Synthesis of [ 15963-40-3 ]

[ 15963-40-3 ] Synthesis Path-Downstream 1~55

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of [ 15963-40-3 ]

Alkenyls

Aliphatic Cyclic Hydrocarbons

Esters

Precautionary Statements-General

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Response

Storage

Disposal

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Health hazards

Environmental hazards

Inquiry

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Related Functional Groups of
[ 15963-40-3 ]