tert-Butyl 4-{4-[(Z)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate → Tert-butyl 4-{4-[2-(naphthalen-1-yl)ethyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

HRID 549945Notes

Reaction equation

HRID 549945 reaction equation
[C:1]1(/[CH:11]=[CH:12]\[C:13]2[N:14]=[C:15]([CH:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)[S:16][CH:17]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1>CO.[Pd]>[C:1]1([CH2:11][CH2:12][C:13]2[N:14]=[C:15]([CH:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)[S:16][CH:17]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 67156180tert-Butyl 4-{4-[(Z)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

Product 1

HCID 67156684Tert-butyl 4-{4-[2-(naphthalen-1-yl)ethyl]-1,3-thiazol-2-yl}piperidine-1-carboxylateYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl 4-{4-[(Z)-2-(naphthalen-1-yl)ethenyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (IV-3, 1.5 g) is dissolved in 90 ml of methanol and, at 30° C., hydrogenated under a hydrogen pressure of 10 bar using 10% Pd/C as catalyst. Removal of the catalyst by filtration and removal of the solvent under reduced pressure gives tert-butyl 4-{4-[2-(naphthalen-1-yl)ethyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.48 g) as a colourless oil.

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-9adc7afb780441da8a430f9dbdc9e3c7
Source dataset
uspto-grants-2011_05
Patent number
US07943774B2

Reaction notes

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