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[ CAS No. 82891-99-4 ] {[proInfo.proName]}

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Chemical Structure| 82891-99-4
Chemical Structure| 82891-99-4
Structure of 82891-99-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 82891-99-4 ]

CAS No. :82891-99-4 MDL No. :MFCD00040621
Formula : C5H9NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :ZYXOSRQIZOOVTN-UHFFFAOYSA-N
M.W : 147.13 Pubchem ID :10888059
Synonyms :

Safety of [ 82891-99-4 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P261-P270-P210-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362-P301+P310+P330-P304+P340+P311-P403+P233-P403+P235-P405 UN#:2810
Hazard Statements:H301+H331-H315-H319-H227 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 82891-99-4 ]

* 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 [ 82891-99-4 ]
  • Downstream synthetic route of [ 82891-99-4 ]

[ 82891-99-4 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 18742-02-4 ]
  • [ 82891-99-4 ]
YieldReaction ConditionsOperation in experiment
38% With sodium nitrite In dimethyl sulfoxide at 0 - 18℃; for 6 h; Inert atmosphere To a solution of commercially available 2-(2-bromoethyl)-1,3-dioxolane (40.73 g, 225 mmol) in anhydrous DMSO (350 mL) was added a solution of NaNO2 (27.95 g, 405 mmol) in anhydrous DMSO (350 mL) slowly at 0°C and the resulting mixture was stirred at 18°C for 6 hours under N2. Then, the reaction mixture was poured into water and extracted with MTBE. The combined organic phase was washed with brine, dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The crude product was purified by silica gel column chromatography to give intermediate 2-(2-nitroethyl)-1,3-dioxolane (12.50 g, 38percent) as a yellow liquid . A mixture of this intermediate (3.97 g, 27 mmol) and tert-butyl 4-formylpiperidine-1-carboxylate (6.61 g, 31) in TEA (3.00 g, 30 mmol) was stirred at 18°C for 8 hours. Then a solution of DMAP (330 mg, 2.70 mmol) in Ac2O (4.13 g, 40 mmol) was added and the reaction mixture was stirred at 18°C for 7 hours. The reaction was quenched with water and then extracted with EtOAc. The combined organic phase was washed with saturated brine, dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel column chromatography to afford intermediate tert-butyl 4-[(Z)-3-(1,3-dioxolan-2-yl)-2-nitro-prop-1-enyl]piperidine-1-carboxylate (5.64 g, 61percent) as a yellow liquid. Finally, a stirred suspension of this intermediate (2.50 g, 7.30 mmol) in absolute EtOH (100 mL) and CHCl3 (8 mL) containing PtO2 (414 mg, 1.83 mmol) was placed under H2 (50 Psi) at 18°C after 15 hours, the mixture was filtered through Celite and washed with EtOH. The filtrate was concentrated to dryness to give desired reagent R-04b (2.02 g, 88percent crude) as a yellow syrup which was used for next step without further purification. ESI-MS (M+1): 315.3 calc. for C16H30N2O4: 314.2.
35% With sodium nitrite In N,N-dimethyl-formamide at 20℃; for 6 h; 2d: To a solution of bromo compound (5.4 g, 30 mmol) in DMF (60 mL) was added NaNO2 (3.5 g, 50 mmol). After stirring at r.t. for 6 h, the reaction mixture was poured into ice-water (60 mL) and layered over with petroleum ether (100 mL). The aqueous phase was extracted with diethyl ether (60 mL .x. 3). The organic phase was dried over anhydrous Na2SO4, filtered, concentrated, and the residue was purified by flash column chromatography on silica gel with 5percent Et2O in hexane as eluent to afford 2d (1.5 g, 35percent) as pale yellow oil. 1H NMR (CDCl3): δ 2.40-2.47 (m, 1H), 3.85-4.02 (m, 4H), 4.51 (t, J = 7.2 Hz, 2H), 5.03 (t, J = 3.6 Hz, 1H).
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 21, p. 4040 - 4045
[2] Journal of the American Chemical Society, 1986, vol. 108, p. 2662
[3] Tetrahedron, 1984, vol. 40, # 19, p. 3809 - 3814
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 11, p. 3427 - 3430
[5] Patent: WO2017/85053, 2017, A1, . Location in patent: Page/Page column 55
[6] Journal of Fluorine Chemistry, 2012, vol. 133, p. 108 - 114
[7] Journal of Organic Chemistry, 1990, vol. 55, # 15, p. 4585 - 4595
[8] Letters in Organic Chemistry, 2017, vol. 14, # 1, p. 39 - 42
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  • [ 58657-26-4 ]
  • [ 107-21-1 ]
  • [ 82891-99-4 ]
Reference: [1] Synthesis, 1986, # 7, p. 535 - 538
[2] Patent: US2007/260057, 2007, A1, . Location in patent: Page/Page column 13
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