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[ CAS No. 1312412-87-5 ]

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2D
Chemical Structure| 1312412-87-5
Chemical Structure| 1312412-87-5
Structure of 1312412-87-5 *Storage: {[proInfo.prStorage]}

Quality Control of [ 1312412-87-5 ]

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Product Details of [ 1312412-87-5 ]

CAS No. :1312412-87-5MDL No. :MFCD24471390
Formula : C10H14BrNO4 Boiling Point : 403.6±45.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :292.13Pubchem ID :69919790
Synonyms :

Computed Properties of [ 1312412-87-5 ]

TPSA : 63.7 H-Bond Acceptor Count : 4
XLogP3 : 1.4 H-Bond Donor Count : 0
SP3 : 0.70 Rotatable Bond Count : 2

Safety of [ 1312412-87-5 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1312412-87-5 ]

  • Upstream synthesis route of [ 1312412-87-5 ]
  • Downstream synthetic route of [ 1312412-87-5 ]

[ 1312412-87-5 ] Synthesis Path-Upstream   1~3

  • 1
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  • [ 1312412-87-5 ]
YieldReaction ConditionsOperation in experiment
99% With N-Bromosuccinimide In tetrachloromethane at 10 - 15℃; for 2.00 h; To a stirred solution of tert-butyl 2,4-dioxopiperidine-1-carboxylate (1 g, 4.69 mmol) in dry CCl4 (10 mL), N-bromosuccinimide (0.83 g, 4.69 mmol) was added at 10 °C. The reaction mixture was stirred at 10-15 °C for 2 h. It was then evaporated under reduced pressure. Water (10 mL) was added and the desired product was extracted with EtOAc (2 x 30 mL). The combined organic layer was dried over Na2SO4 and concentrated. The resulting crude product was purified by flash column chromatography, affording the title product. Yield: 99percent (1.4 g, off white solid). 1H NMR (400 MHz, DMSO-d6): δ 5.50 (s, 1H), 3.74-3.71 (m, 2H), 2.69-2.66 (m, 2H), 1.46 (s, 9H). LCMS: (Method A) 193.8 (M-Boc+H), Rt. 2.93min, 81 .51 percent (Max).
99% With N-Bromosuccinimide In tetrachloromethane at 10 - 15℃; for 2.00 h; To a stirred solution of tert-butyl 2,4-dioxopiperidine-1-carboxylate (1 g, 4.69 mmol) in dry Cd4 (10 mL), N-bromosuccinimide (0.83 g, 4.69 mmol) was added at 10°C. The reaction mixture was stirred at 10-15°C for 2 h. It was then evaporated under reducedpressure. Water (10 mL) was added and the desired product was extracted with EtOAc(2 x 30 mL). The combined organic layer was dried over Na2504 and concentrated.The resulting crude product was purified by flash column chromatography, affording thetitle product. Yield: 99percent (1.4 g, off white solid). 1H NMR (400 MHz, DMSO-d6): 65.50(s,IH),3.74-3.71 (m, 2H), 2.69-2.66 (m, 2H), 1.46 (s, 9H). LCMS: (Method A) 193.8(M-Boc+H), Rt. 2.93mm, 81 .51percent (Max).
99% With N-Bromosuccinimide In tetrachloromethane at 10 - 15℃; for 2.00 h; To a stirred solution of tert-butyl 2,4-dioxopiperidine-1-carboxylate (1 g, 4.69 mmol) in dry Cd4 (10 mL), N-bromosuccinimide (0.83 g, 4.69 mmol) was added at 10 °C. The reaction mixture was stirred at 10-15 °C for 2 h. It was then evaporated under reduced pressure. Water (10 mL) was added and the desired product was extracted with EtOAc (2 x 30 mL). The combined organic layer was dried over Na2SO4 and concentrated. The resulting crude product was purified by column chromatography, affording the title product. Yield: 99percent(1.4 g, off white solid). 1H NMR (400 MHz, DMSO-d6): 6 5.50 (s,IH), 3.74-3.71 (m, 2H),2.69-2.66 (m, 2H), 1.46 (5, 9H). LCMS: (Method A) 193.8 (M-Boc+H), Rt. 2.93mm, 81 .51percent (Max).
99% With N-Bromosuccinimide In tetrachloromethane at 10 - 15℃; for 2.00 h; To a stirred solution of tert-butyl 2,4-dioxopiperidine-1-carboxylate (1 g, 4.69 mmol) in dry CCI4 (10 mL), N-bromosuccinimide (0.83 g, 4.69 mmol) was added at 10 °C. The reaction mixture was stirred at 10-15 °C for 2 h. It was then evaporated under reduced pressure. Water (10 mL) was added and the desired product was extracted with EtOAc (2 x 30 mL). The combined organic layer was dried over Na2SO4 and concentrated. The resulting crude product was purified by column chromatography, affording the title product. Yield: 99percent (1.4 g, off white solid). 1H NMR (400 MHz, DMSO-d6): δ 5.50 (s,1 H), 3.74-3.71 (m, 2H), 2.69-2.66 (m, 2H), 1.46 (s, 9H). LCMS: (Method A) 193.8 (M-Boc+H), Rt. 2.93min, 81.51 percent (Max).
55% With N-Bromosuccinimide In tetrachloromethane at 10 - 15℃; for 2.00 h; To a mixture of 2,4-dioxo-piperidine-l-carboxylic acid tert-butyl ester (40 g, 187.58 mmol) in carbon tetrachloride (500 mL) was added N-bromosuccinimide (33.38 g, 187.58 mmol) portionwise keeping the reaction temperature in the range of 10°C-15°C. The mixture was further stirred at 10°C-15°C for 2 hours. The reaction mixture was allowed to warm to room temperature and the solvents evaporated in vacuo. The residue thus obtained was dissolved in AcOEt and washed with H20. The organic layer was separated, dried (Na2S04), filtered and the solvents evaporated in vacuo to yield 30 g (55percent) of racemic intermediate 1 that was used in the next step without further purification.
55% With N-Bromosuccinimide In tetrachloromethane at 10 - 15℃; To a mixture of 2,4-dioxo-piperidine-l-carboxylic acid tert-butyl ester (40 g, 187.58 mmol) in carbon tetrachloride (500 mL) was added N-bromosuccinimide (33.38 g, 187.58 mmol) portionwise keeping the reaction temperature in the range of 10°C-15°C. The mixture was further stirred at 10°C-15°C for 2 hours. The reaction mixture was allowed to warm to room temperature and the solvents evaporated in vacuo. The residue thus obtained was dissolved in AcOEt and washed with H20. The organic layer was separated, dried (Na2S04), filtered and the solvent evaporated in vacuo to yield 30 g (55percent) of racemic intermediate 2 that was used in the next step without further purification.
29% With N-Bromosuccinimide In tetrachloromethane at 0 - 20℃; for 2.00 h; Step iii: tert-butyl 3-bromo-2,4-dioxopiperidine-l-carboxylate
To a 100 mL round bottom flask, were added tert-butyl 2,4-dioxopiperidine-l-carboxylate (3 g, 0.014 mol) and carbon tetrachloride (50 mL). The reaction mixture was cooled to 0 °C. To the same flask, NBS (3 g, 0.0168 mol) was added portion wise. The reaction mixture was stirred at RT for 2 h. The reaction mixture was diluted with dichloromethane and washed with water. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to get the title compound [1.2 g, 29 percent]. The obtained title compound was used in next step without any further purification. LCMS: 191.8 (M-Boc+l)+.

Reference: [1] Patent: WO2016/30443, 2016, A1. Location in patent: Page/Page column 96
[2] Patent: WO2017/144637, 2017, A1. Location in patent: Page/Page column 36
[3] Patent: WO2017/144633, 2017, A1. Location in patent: Page/Page column 100; 101
[4] Patent: WO2017/144639, 2017, A1. Location in patent: Page/Page column 85-86
[5] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 14, p. 4037 - 4043
[6] Patent: WO2011/73339, 2011, A1. Location in patent: Page/Page column 42
[7] Patent: WO2011/73347, 2011, A1. Location in patent: Page/Page column 32-33
[8] Patent: WO2015/101928, 2015, A1. Location in patent: Page/Page column 52; 53; 54
[9] Patent: US2012/252800, 2012, A1. Location in patent: Page/Page column 14
[10] Journal of Medicinal Chemistry, 2013, vol. 56, # 18, p. 7243 - 7259
[11] Patent: WO2014/113191, 2014, A1. Location in patent: Paragraph 0146; 0147
[12] Patent: WO2017/144635, 2017, A1. Location in patent: Page/Page column 41; 42
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Reference: [1] Patent: WO2014/113191, 2014, A1
[2] Patent: WO2015/101928, 2015, A1
  • 3
  • [ 24424-99-5 ]
  • [ 1312412-87-5 ]
Reference: [1] Patent: WO2015/101928, 2015, A1
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