Potassium Carbonate → (1-Thiiranylmethyl-piperidin-4-yl)-carbamic acid tert-butyl ester

HRID 1019953Notes

Reaction equation

HRID 1019953 reaction equation
[CH2:1]1[S:3][CH:2]1[CH2:4]Cl.[C:6]([O:10][C:11](=[O:19])[NH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:9])([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:6]([O:10][C:11](=[O:19])[NH:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:4][CH:2]2[CH2:1][S:3]2)[CH2:15][CH2:14]1)([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18588EpithiochlorohydrinHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 86662008(1-Thiiranylmethyl-piperidin-4-yl)-carbamic acid tert-butyl esterYield 114%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Epithiochlorohydrine (268 mg, 2.40 mmol, 1.0 eq) is added at room temperature to a stirred solution of piperidin-4-yl-carbamic acid tert-butyl ester (500 mg, 2.40 mmol, 1.0 eq) in N,N-dimethylformamide (15 mL), followed by potassium carbonate (335 mg, 2.40 mmol, 1.0 eq). After 24 hours stirring at room temperature, solvent is evaporated and the residue is extracted with dichloromethane (3×20 mL) and water (20 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford (1-thiiranylmethyl-piperidin-4-yl)-carbamic acid tert-butyl ester as a white solid (745 mg, 57% yield).

Workup

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with dichloromethane (3×20 mL) and water (20 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1f08cec811ef4ec28998c6ab2d44f353
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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