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[ CAS No. 53292-90-3 ]

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Chemical Structure| 53292-90-3
Chemical Structure| 53292-90-3
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CAS No. :53292-90-3 MDL No. :MFCD01862294
Formula : C12H21NO4 Boiling Point : 396.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :243.30 g/mol Pubchem ID :-
Synonyms :

Safety of [ 53292-90-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53292-90-3 ]

  • Upstream synthesis route of [ 53292-90-3 ]
  • Downstream synthetic route of [ 53292-90-3 ]

[ 53292-90-3 ] Synthesis Path-Upstream   1~6

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  • [ 62456-15-9 ]
Reference: [1] ACS Combinatorial Science, 2017, vol. 19, # 5, p. 286 - 298
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  • [ 223131-01-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 16, p. 2177 - 2180
[2] Patent: US2016/333021, 2016, A1, . Location in patent: Page/Page column 0432
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  • [ 247570-24-7 ]
Reference: [1] Patent: WO2008/57468, 2008, A1,
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  • [ 67-56-1 ]
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  • [ 146307-51-9 ]
Reference: [1] Chimia, 2005, vol. 59, # 3, p. 72 - 76
[2] ACS Combinatorial Science, 2017, vol. 19, # 5, p. 286 - 298
  • 5
  • [ 53292-90-3 ]
  • [ 239074-29-4 ]
YieldReaction ConditionsOperation in experiment
96.6% With dimethylsulfide borane complex In tetrahydrofuran at -10 - 15℃; for 4 h; Inert atmosphere Step A: tert-butyl N- [(ir, 4r)-4-(Hydroxymethyl)cyclohexyl] carbamate. To a 20-L 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen wasplaced (ir, 4r)-4-[[(tert-butoxy)carbonyl]amino]cyclohexane- 1 -carboxylic acid (1066 g, 4.38 mol, 1.00 equiv) and THF (10 L). This was followed by the dropwise addition of BH3-Me25 (10M, 660 mL) at -10 °C over 1 h. The resulting solution was stirred for 3 h at 15 °C. This reaction was performed three times in parallel and the reaction mixtures were combined. The reaction was then quenched by the addition of methanol (2 L). The resulting mixture was concentrated under vacuum. This resulted in of tert-butyl N-[(lr, 4r)-4-(hydroxymethyl)cyclohexyl]carbamate(3000 g, 99.6percent) as a white solid. MS (ESI): mass calcd. for C12H23N03, 229.32; m/z found,215.2 [M-tBu+MeCN+H] ‘H NMR: (300 IVIFIz, CDC13): 4.40 (s, 1H), 3.45 (d, J 6.3 Hz,2H), 3.38 (s, 1H), 2.05-2.02 (m, 2H), 1.84-1.81 (m, 2H), 1.44 (s, 11H), 1.17-1.01 (m, 4H)
3.5 kg With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 0 - 30℃; for 6 h; Large scale In the 50 L reaction kettle, adding 5 kg of trans - 4 - Boc - amino-cyclohexane carboxylic acid, 20 kg of tetrahydrofuran, 10 kilograms of sodium borohydride. Control temperature, stirring in batches under the adding 15 liter 1 M boron trifluoride ether solution. Control temperature at 0 - 10 degrees, reaction 1 hours, after up to 30 degrees, the reaction 5 hours. Concentrated off solvent, adding water, stirring, precipitated solid, filtering, to obtain 3.5 kg trans - 4 - Boc - amino-cyclohexane methanol
Reference: [1] Patent: WO2018/112382, 2018, A1, . Location in patent: Page/Page column 109; 110
[2] Patent: EP1961744, 2008, A1, . Location in patent: Page/Page column 100
[3] Patent: WO2010/45987, 2010, A1, . Location in patent: Page/Page column 44
[4] Patent: US2016/333021, 2016, A1, . Location in patent: Paragraph 1158
[5] Patent: CN107011216, 2017, A, . Location in patent: Paragraph 0024; 0025
[6] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 2, p. 89 - 93
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  • [ 1313279-48-9 ]
Reference: [1] Patent: WO2018/112382, 2018, A1,
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