Tert-butyl 4-hydroxypiperidine-1-carboxylate → HCID 49759211, compound

HRID 1879643Notes

Reaction equation

HRID 1879643 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.CC(C)([O-])C.[K+].F[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[C:24]([O:31][CH3:32])[CH:23]=1>O1CCCC1>[CH3:32][O:31][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[N+:28]([O-:30])=[O:29])[O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 27792505-Fluoro-2-nitroanisoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 49759211HCID 49759211, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of tert-butyl 4-hydroxypiperidine-1-carboxylate (1.49 g) and tetrahydrofuran (30 mL), potassium tert-butoxide (830 mg) was added under ice cooling and stirred for 30 minutes, followed by addition of a mixture of 4-fluoro-2-methoxy-1-nitrobenzene (1.00 g) and tetrahydrofuran (20 mL). After stirring at room temperature for 3 hours, the reaction mixture was extracted by addition of water and ethyl acetate, washed with saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; n-hexane:diethyl ether=4:1) to give tert-butyl 4-(3-methoxy-4-nitrophenoxy)piperidine-1-carboxylate (898 mg).

Workup

  1. additionwas added under ice cooling
  2. stirringAfter stirring at room temperature for 3 hours
  3. extractionthe reaction mixture was extracted by addition of water and ethyl acetate
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent; n-hexane:diethyl ether=4:1)

Sources & evidence

ORD record
ord-81bd906ac1ce4334a3d0cb42c221f60c
Source dataset
uspto-grants-2012_11
Patent number
US08318702B2

Reaction notes

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