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CAS No. :1572-98-1 MDL No. :MFCD00034667
Formula : C7H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :FYGRPGOHQCPZCV-UHFFFAOYSA-N
M.W : 141.17 Pubchem ID :344887
Synonyms :

Safety of [ 1572-98-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P261-P270-P210-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312-P403+P235 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H227 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1572-98-1 ]

* 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.

  • Upstream synthesis route of [ 1572-98-1 ]
  • Downstream synthetic route of [ 1572-98-1 ]

[ 1572-98-1 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 1572-98-1 ]
  • [ 26734-09-8 ]
Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 24, p. 4907 - 4911
[2] Chemistry - A European Journal, 2012, vol. 18, # 5, p. 1383 - 1400
[3] Journal of Heterocyclic Chemistry, 1971, vol. 8, p. 961 - 966
[4] Advanced Synthesis and Catalysis, 2014, vol. 356, # 5, p. 1113 - 1118
[5] Russian Chemical Bulletin, 2014, vol. 63, # 2, p. 409 - 415[6] Izvestiya Akademii Nauk. Seriya Khimicheskaya, 2014, vol. 2, p. 409 - 415,7
  • 2
  • [ 1572-98-1 ]
  • [ 19295-57-9 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 3 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran
1)
3-hydroxy-2,2-dimethylpropanenitrile
To a mixture of ethyl 2-cyano-2-methylpropionate (5.0 g, 35.4 mmol), tetrahydrofuran (40 ml) and water (100 ml), sodium borohydride (4.47 g, 106 mmol) was slowly added, and the mixture was stirred at room temperature for 3 hr. 6N hydrochloric acid was added to the reaction mixture to quench the reaction, and the mixture was extracted with ethyl acetate.
The extract was washed with water, dried over anhydrous magnesium sulfate, passed through a small amount of silica gel and concentrated under reduced pressure to give the title compound (3.4 g, yield 97percent) as an oil.
1H-NMR (CDCl3): δ 1.36 (6H, s), 3.58 (2H, s).
97%
Stage #1: With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 3 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water
To a mixture of ethyl 2-cyano-2-methylpropionate (5.0 g, 35.4 mmol), tetrahydrofuran (40 ml) and water (100 ml), sodium borohydride (4.47 g, 106 mmol) was slowly added, and the mixture was stirred at room temperature for 3 hr. 6N hydrochloric acid was added to the reaction mixture to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, passed through a small amount of silica gel and concentrated under reduced pressure to give the title compound (3.4 g, yield 97percent) as an oil.
63%
Stage #1: With lithium borohydride In tetrahydrofuran at 20℃; for 0.5 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water
Under an atmosphere of nitrogen, a tetrahydrofuran (200 ml) solution of 28.2 g (0.20 mol) of cyano-dimethylacetic acid ethyl ester (1-70) was added dropwise to a tetrahydrofuran (500 ml) solution of 4.8 g (0.22 mol) of lithium borohydride spending 30 minutes, and then the mixture was stirred overnight at room temperature. By adding 6 N hydrochloric acid to the reaction solution, separation of layers was effected, the aqueous layer was extracted with ethyl acetate, combined with the first organic layer, washed with brine and then dried over magnesium sulfate. The solvent was evaporated, ether was added to the resulting residue, the insoluble material was removed by filtration, and then the solvent of the filtrate was evaporated. The thus obtained residue was applied to a silica gel column chromatography, and 12.5 g (63percent) of the title compound was obtained as a colorless oily substance from a n-hexane-ethyl acetate (2:1 v/v) eluate. 1H-NMR (CDCl3)δ: 1.36 (6H, s), 2.26 (1H, brs), 3.58 (2H, s).
55.09% With sodium tetrahydroborate In methanol at 0 - 20℃; To a solution of ethyl 2-cyano-2-methylpropanoate (10.34 g, 73.25 mmol) in methanol(200 mL) were added NaBH4 (5.54 g, 146 mmol) in portions at 0 °C. Then the mixture wasstirred at room temperature overnight. The mixture was adjusted to pH = 7~8 with saturatedNH4Cl aqueous solution, and then extracted with EtOAc (100mL x 3). The combined organiclayers were washed with brine (150mL), dried over Na2S04, filtered and concentrated in vacuo.The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) =20/1 to 10/1)to give the title compound as colorless oil (4.0 g, yield 55.09percent).1HNMR (400 MHz, CDCb) 8 (ppm): 3.44 (d, J= 6.3 Hz, 2H), 1.23 (s, 6H).
55.09% at 20℃; 0 ° C,To 2-cyano-2-methylpropionic acidEthyl ester (10.34 g, 73.25 mmol)In methanol (200 mL) was added NaBH4 (5.54 g, 146 mmol) in portions.The reaction was stirred overnight at room temperature.After the reaction,The reaction solution was adjusted to pH = 7 to 8 with saturated aqueous ammonium chloride solution,Then extracted with EtOAc (100 mL x 3).The combined organic phases were washed with saturated brine (150 mL)Dried over anhydrous sodium sulfate,Filtered and concentrated under reduced pressure.The resulting residue was purified by silica gel column chromatography (PE / EtOAc (v / v) = 20/1 to 10/1)The title compound was obtained as a colorless oil (4.0 g, yield 55.09percent).
1 g With sodium tetrahydroborate; water In tetrahydrofuran at 20℃; for 6 h; Description 933-llydroxy-2,2-dimethylpropanenitrile (D93)To a mixture of ethyl 2-cyano-2-methylpropanoate (2.5 g) in THF (20 mL) and water (50 mL) was added NaBH4 (3.35 g) portionwise. After addition the mixture was stirred at RT for 6 hours. Hydrochloric acid (6 M) was added to quench the reaction mixture, and then extracted with EtOAc(50 mL). The extract was washed with water (50 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the title compound (1 g). 1H NMR (400 MHz, MeOD-d4): 5.45 (s, 1H), 3.36 (s, 2H), 1.21 (s, 6H).Description 94

Reference: [1] Patent: US2009/156582, 2009, A1, . Location in patent: Page/Page column 35
[2] Patent: EP1847531, 2007, A1, . Location in patent: Page/Page column 51
[3] Patent: EP1717238, 2006, A1, . Location in patent: Page/Page column 61
[4] Patent: WO2017/48675, 2017, A1, . Location in patent: Paragraph 0434
[5] Patent: CN106478651, 2017, A, . Location in patent: Paragraph 0900; 0901; 0902
[6] Patent: US2007/299111, 2007, A1, . Location in patent: Page/Page column 33
[7] Patent: WO2007/28051, 2007, A2, . Location in patent: Page/Page column 49-50
[8] Patent: WO2015/180612, 2015, A1, . Location in patent: Page/Page column 68
  • 3
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  • [ 324763-51-1 ]
Reference: [1] Patent: WO2011/148392, 2011, A1,
[2] Patent: WO2012/21446, 2012, A2,
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 3, p. 957 - 971
  • 4
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  • [ 22426-30-8 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: at 20℃; for 1 h;
Preparation Example A4-3: 2-cyano-2-methylpropanoyl chloride; [536] To a solution of commercially available ethyl-2-cyano-2-methylpropanoate (3.5g, 24.8mmol) in methanol (10 ml) was added LiOH (900mg, 37.2mmol) and water (0.5ml), and reacted at rt for 1 h. After the reaction finished, the solvent was con- <n="32"/>centrated in vacuo, IN-HCl (50ml) was added, and extracted with EtOAc. The extracted organic layer was dried over MgSO 4 , concentrated in vacuo to give2-cyano-2-methylpropionic acid (2.67g, 95percent). This compound (2.5g, 22mmol) was dissolved in DCM (7 ml), and reacted according to the procedure described in Step B of Preparation Example A4-1 to give the title compound (2.5g, 86.3percent).
73% With potassium hydroxide In water at 40℃; for 2 h; To a vial was added ethyl 2-cyano-2-methylpropanoate (1.0 g, 7.08 mmol), water (5 mL) and KOH (795 mg, 14.1 mmol).
The mixture was stirred at 40° C. for 2 hours.
The reaction mixture was concentrated to remove methanol, acidified to pH 5 with 1 N HCl and extracted with ethyl acetate (50 ml*2).
The combined organic layers were washed with brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo to give 2-cyano-2-methyl-propanoic acid (600 mg, 73percent yield) as a pale-yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 13.59 (br, 1H), 1.52 (s, 6H).
Reference: [1] Patent: WO2008/7930, 2008, A1, . Location in patent: Page/Page column 30-31
[2] Synthesis, 2005, # 4, p. 569 - 574
[3] Patent: US2018/282328, 2018, A1, . Location in patent: Paragraph 0832; 0833
[4] Chemische Berichte, 1932, vol. 65, p. 432,441
[5] Journal of the American Chemical Society, 1916, vol. 38, p. 911
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  • [ 105-56-6 ]
  • [ 77-78-1 ]
  • [ 1572-98-1 ]
  • [ 72291-30-6 ]
Reference: [1] Patent: WO2012/21446, 2012, A2, . Location in patent: Page/Page column 29
  • 6
  • [ 105-56-6 ]
  • [ 74-88-4 ]
  • [ 1572-98-1 ]
  • [ 72291-30-6 ]
Reference: [1] Patent: EP1717238, 2006, A1, . Location in patent: Page/Page column 60
  • 7
  • [ 1572-98-1 ]
  • [ 180181-02-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 11, p. 1171 - 1173
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