Methanethioamide → Tert-butyl 4-(1,3-thiazol-4-yl)piperidine-1-carboxylate

HRID 1804598Notes

Reaction equation

HRID 1804598 reaction equation
Br[CH2:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=O.[CH:18]([NH2:20])=[S:19]>C1COCC1.C(OCC)(=O)C>[S:19]1[CH:2]=[C:3]([CH:5]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[N:20]=[CH:18]1

Participants

5

Reactant 2

HCID 3005587MethanethioamideHCID 18187487tert-Butyl 4-(2-Bromoacetyl)piperidine-1-carboxylate

Product 1

HCID 53485228Tert-butyl 4-(1,3-thiazol-4-yl)piperidine-1-carboxylateYield 63%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

The title compound from Step B above (500 mg, 1.63 mmol) was combined with thioformamide (100 mg, 1.63 mmol) in 5 mL of THF, warmed to 60° C., and stirred overnight. The mixture was cooled to RT and diluted with ethyl acetate. The solution was then washed with water followed by brine. The organics were dried over magnesium sulfate, filtered and concentrated under vacuum. Purification via preparative TLC plates (3×1000 μM) eluting with 60% ethyl acetate/hexane afforded the title compound (282 mg, 63%) as a clear oil. ESI-MS calculated for C13H20N2O2S: Exact Mass: 268.12. Found: 169.12 (M-Boc)+ and 291.14 (MNa)+.

Workup

  1. temperatureThe mixture was cooled to RT
  2. washThe solution was then washed with water
  3. dry with materialThe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customPurification via preparative TLC plates (3×1000 μM)
  7. washeluting with 60% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ea6c954d703d44fea793abfa1aa76855
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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