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[ CAS No. 403802-41-5 ] {[proInfo.proName]}

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Chemical Structure| 403802-41-5
Chemical Structure| 403802-41-5
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Product Details of [ 403802-41-5 ]

CAS No. :403802-41-5 MDL No. :MFCD24469756
Formula : C13H21NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :FUIPHCXERBVLBP-UHFFFAOYSA-N
M.W : 239.31 Pubchem ID :69786345
Synonyms :

Safety of [ 403802-41-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 403802-41-5 ]

* 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 [ 403802-41-5 ]
  • Downstream synthetic route of [ 403802-41-5 ]

[ 403802-41-5 ] Synthesis Path-Upstream   1~3

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  • [ 156185-63-6 ]
Reference: [1] Patent: US2002/68753, 2002, A1,
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Reference: [1] Patent: WO2012/173917, 2012, A1, . Location in patent: Page/Page column 40
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 8, p. 936 - 941
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YieldReaction ConditionsOperation in experiment
86% With n-butyllithium; paraformaldehyde In tetrahydrofuran; hexane 12.4
[following conditions described in: Marshall, James A.; Bartley, Gary S.; Wallace, Eli M. Total Synthesis of the Pseudopterane (-)-Kallolide B, the Enantiomer of Natural (+)-Kallolide B. J. Org. Chem. (1996), 61(17), 5729-5735.
And Baker, Raymond; Boyes, Alastair L.; Swain, Christopher J.
Synthesis of talaromycins A, B, C, and E. J. Chem. Soc., Perkin Trans. 1 (1990), (5), 1415-21.)]
A solution of 6.0 g (16.3 mmol) of 4-(2,2-Dibromo-vinyl)-piperidine-1-carboxylic acid tert-butyl ester in 150 ml THF was treated at -78° C. with 21.4 ml (34.2 mmol) of n-BuLi (ca 1.6 M in hexane).
After 2 h at this temperature 4.9 g (16.3 mmol) of paraformaldehyde were added.
The reaction was warmed up to RT for 3 h and after 1 h at this temperature partitioned between water/ether (3*).
The organic phases were washed with aqueous 10percent NaCl, dried over Na2SO4 and evaporated.
Purification by flash-chromatography on silica gel (hexane/EtOAc 4:1) gave 3.34 g (86percent) of 4-(3-Hydroxy-prop-1-ynyl)-piperidine-1-carboxylic acid tert-butyl ester, MS: 239 (M).
Reference: [1] Patent: US2002/68753, 2002, A1,
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