Trifluoro-methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohex-1-enyl ester synthesis

6synthesis methods

Product Name:Trifluoro-methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohex-1-enyl ester
CAS Number:849069-49-4
Molecular formula:C12H18F3NO5S
Molecular Weight:345.34

37595-74-7 Synthesis

N-Phenyl-bis(trifluoromethanesulfonimide)

37595-74-7
419 suppliers
$5.00/1g

179321-49-4
306 suppliers
$5.00/1g

Trifluoro-methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohex-1-enyl ester

849069-49-4
18 suppliers
$393.00/250mg

Yield:849069-49-4 71.6%

Reaction Conditions:

Stage #1: N-(tert-butoxycarbonyl)-4-aminocyclohexanonewith lithium hexamethyldisilazane in tetrahydrofuran at -78; for 1 h;Inert atmosphere;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide in tetrahydrofuran at 15; for 16 h;Inert atmosphere;

Steps:

48A Example 48A 4-((tert-butoxycarbonyl)amino)cyclohex-1-en-1-yl trifluoromethanesulfonate

Example 48A
4-((tert-butoxycarbonyl)amino)cyclohex-1-en-1-yl trifluoromethanesulfonate
To a solution of tert-butyl (4-oxocyclohexyl)carbamate (1 g, 4.689 mol) in THF (20 mL) was added dropwise LiHMDS (1 M, 9.4 ml, 9.378 mmol) at -78° C. under N₂ atmosphere.
After stirring at -78° C. for 1 h, a solution of (CF₃SO₂)₂NPh (1.84 g, 5.158 mmol) in THF (5 mL) was added.
The mixture was stirred at 15° C. for 16 h, and then quenched with aq NH₄Cl solution (20 mL).
The aqueous layer was extracted with EtOAc (20 mL*2).
The combined organic layers were washed with water, brine, dried over Na₂SO₄, filtered and evaporated.
The residue was purified by column chromatograph on silica gel to provide the title compound as a white solid (1.16 g, yield: 71.60%). LCMS (ESI) m/z: 347 (M+1).