Water → 1-(tert-Butoxycarbonyl)-3-[(4-phenylthiazol-2-yl)thiomethyl]piperidine

HRID 602184Notes

Reaction equation

HRID 602184 reaction equation
[SH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.C(=O)([O-])[O-].[K+].[K+].[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH2:29][CH:28]([CH2:32]I)[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].O>CN(C)C=O>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH2:29][CH:28]([CH2:32][S:1][C:2]2[S:3][CH:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:6]=2)[CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 20716152Tert-butyl 3-(iodomethyl)piperidine-1-carboxylateHCID 1785278304-phenyl-1,3-thiazole-2-thiol

Product 1

HCID 589926811-(tert-Butoxycarbonyl)-3-[(4-phenylthiazol-2-yl)thiomethyl]piperidineYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Mercapto-4-phenylthiazole (304 mg, 1.54 mmol) and potassium carbonate (261 mg, 1.85 mmol) were added to 1-(tert-butoxycarbonyl)-3-iodomethylpiperidine (500 mg, 1.54 mmol) in N,N-dimethylformamide (5 mL). The mixture was stirred at room temperature for 30 min. Subsequently, water was added and the mixture was extracted with ethyl acetate. The extract was then washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=40:1->10:1) gave 598 mg (99%) of the desired compound as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was then washed with brine
  3. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  4. customPurification of the resulting residue by silica gel column chromatography (hexane:ethyl acetate=40:1->10:1)

Sources & evidence

ORD record
ord-46c54148ff874ad0bba0413cd58654ad
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

Loading…