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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 : |
|
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: |
* 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.
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.34 g (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 10% NaCl, dried over Na2SO4 and evaporated. Purification by flash-chromatography on silica gel (hexane/EtOAc 4:1) gave 3.34 g (86%) of 4-(3-Hydroxy-prop-1-ynyl)-piperidine-1-carboxylic acid tert-butyl ester, MS: 239 (M). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.05 g (90%) | With pyridine; dmap; In dichloromethane; water; | 12.5 A solution of 3.34 g (13.96 mmol) of <strong>[403802-41-5]4-(3-Hydroxy-prop-1-ynyl)-piperidine-1-carboxylic acid tert-butyl ester</strong> in 100 ml CH2Cl2 was treated at 0 C. with 1.2 ml (15.4 mmol) of methanesulfonylchloride, 1.7 ml (20.93 mmol) of pyridine and 1.71 g (13.96 mmol) of DMAP. The reaction mixture was warmed up to RT for 3 h, treated with water (10 ml) and stirred for 5 min. After extraction with aqueous 10% KHSO4/Et2O (3*), the organic phases were washed with aqueous saturated NaHCO3 (2*), aqueous 10% NaCl, dried over Na2SO4 and evaporated to give 4.05 g (90%) of 4-(3-Methanesulfonyloxy-prop-1-ynyl)-piperidine-1-carboxylic acid tert-butyl ester, MS: 317 (M). |
With dmap; triethylamine; In dichloromethane; at 5 - 20℃; for 18.0h;Inert atmosphere; | Methanesulfonyl chloride (1 mL; 12.8 mmol) was added dropwise to a solution of 1 - piperidinecarboxylic acid, 4-(3-hydroxy-1 -propyn-1-yl)-, 1 ,1 -dimethylethyl ester (2 g; 8.5 mmol), triethylamine (1.8 mL; 12.8 mmol) and 4-dimethylaminopyridine (10.4 g; 85 mmol) in DCM (20 mL) at 5C under a N2 flow. The temperature pof the reaction mixture was allowed to rise to room temperature for 18 hours. The reaction mixture was poured out into ice water and DCM was added. The organic layer was separated, dried(MgS04), filtered and the solvent was evaporated to dryness to give 1 .41 g of intermediate 91 used without further purification for the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step B: tert-butyl 4-(3 -hydroxyprop- 1 -vn- 1 -vDpiperidine- 1 -carboxylateProduct from step A (0.5 g, 1.355 mmol) was dissolved in dry THF (4.99 ml, 61.0 mmol) under nitrogen. The solution was cooled in a bath at -45C and to it was added «-BuLi (1.6M in hexanes, 1.736 ml, 2.78 mmol) over ca. 2 min. The solution was stirred at -45C to -38C for 45 min, then paraformaldehyde (0.122 g, 4.06 mmol) was added. The suspension was allowed to warm slowly to room temp. After stirring at room temp overnight, the reaction was quenched with aqueous 10% NH4C1 and extracted with ethyl acetate. The organic layer was washed with water and evaporated to yield a crude material which was subjected to silica gel chromatography (gradient elution 9% to 70% EtOAc in hexanes) to provide the desired product. NMR (400 MHz, CDC13) delta 4.46 (d, 2H), 3.80-3.68 (m, 2H), 3.22-3.11 (m, 2H), 2.68-2.58 (m, 1H), 1.86-1.75 (m, 2H), 1.64-1.53 (m, 2H), 1.49 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With quinoline; hydrogen;Lindlar's catalyst; In ethyl acetate; under 760.051 Torr; for 0.666667h; | Step C: fe -butyl 4- [( 1 Z -3 -hydroxyprop- 1 -en- 1 -yllpiperidine- 1 -carboxylateH2, quinolineThe alkyne from step B (6.5 g, 27.2 mmol) and quinoline (0.55 mL, 4.62 mmol) were dissolved in EtOAc (120 mL). Lindlar's catalyst (740 mg) was added and the reaction was stirred under hydrogen atmosphere (1 atm) for 40 minutes. The reaction was filtered and concentrated to yield a crude residue which was purified by silica gel chromatography (gradient elution, 0% to 100% EtOAc in hexanes) to yield the desired allylic alcohol. 1H NMR (500 MHz, CDC13) delta 5.58 (m, 1H), 5.37 (dd, J 10.8 & 9.6 Hz, 1H), 4.22 (d, 2H), 4.16-3.99 (m, 2H), 2.80-2.78 (m, 2H), 2.52-2.40 (m, 1H), 1.61-1.56 (m, 2H), 1.45 (s, 9H), 1.36-1.22 (m, 2H). |
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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