Potassium Carbonate → HCID 59860244, compound

HRID 419539Notes

Reaction equation

HRID 419539 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([OH:8])[CH2:3]1.[CH3:9][O:10][C:11]1[CH:16]=[C:15](F)[CH:14]=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C(OCC)C.[Cl-].[Na+]>[CH3:9][O:10][C:11]1[CH:16]=[C:15]([N:2]2[CH2:7][CH2:6][CH2:5][C@H:4]([OH:8])[CH2:3]2)[CH:14]=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27792505-Fluoro-2-nitroanisoleHCID 16211918(3S)-Piperidin-3-ol--hydrogen chloride (1/1)

Product 1

HCID 59860244HCID 59860244, compoundYield 78.3%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 5234Sodium ChlorideSolvent

Procedure

A solution of (3S)-3-piperidinol hydrochloride (3.00 g, 21.7 mmol), 5-fluoro-2-nitrophenyl methyl ether (Example 22, step A) (3.38 g, 19.76 mmol) and K2CO3 (9.00 g, 65.22 mmol) in DMSO (75 mL) was stirred overnight. The next morning, the reaction was diluted with diethyl ether and saturated aqueous sodium chloride. The ether layer was washed thrice with H2O, and the combined aqueous layers were subsequently washed twice with diethyl ether. The combined organic layers were dried over Na2SO4, taken to a residue under reduced pressure, and purified by chromatography on SiO2 to give the title compound as a pale yellow solid (3.90 g, 15.47 mmol, 78% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.59-1.71 (m, 2H), 1.79 (s, 1H), 1.86-1.96 (m, J=12.96, 6.41, 6.27, 3.48 Hz, 1H), 1.96-2.04 (m, 1H), 3.13-3.24 (m, 2H), 3.47 (ddd, J=12.59, 6.36, 3.20 Hz, 1H), 3.66 (dd, J=12.82, 3.48 Hz, 1H), 3.86-3.92 (m, J=7.44, 3.94, 3.74, 3.74 Hz, 1H), 3.93 (s, 3H), 6.34 (d, J=2.56 Hz, 1H), 6.43 (dd, J=9.34, 2.38 Hz, 1H), 7.98 (d, J=9.34 Hz, 1H).

Workup

  1. washThe ether layer was washed thrice with H2O
  2. washthe combined aqueous layers were subsequently washed twice with diethyl ether
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. custompurified by chromatography on SiO2

Sources & evidence

ORD record
ord-01d21414a96f4fd888098f6a0728f58a
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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