Potassium Carbonate → Tert-butyl 4-(4-ethynyl-1,3-thiazol-2-yl)piperidine-1-carboxylate

HRID 2199181Notes

Reaction equation

HRID 2199181 reaction equation
[CH:1]([C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[S:6][CH:7]=1)=O.[C:21](=O)([O-])[O-].[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[C:1]([C:3]1[N:4]=[C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[S:6][CH:7]=1)#[CH:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 7172298tert-Butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylateHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 58181284Tert-butyl 4-(4-ethynyl-1,3-thiazol-2-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under argon, tert-butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylate (600 mg) was dissolved in methanol, and potassium carbonate (839 mg) and dimethyl 1-diazo-2-oxopropylphos-phonate (786 mg) were added. The mixture was stirred at room temperature for 3 hours. After aqueous work-up, the mixture was extracted with ethyl acetate, the extracts were dried with sodium sulphate and the solvent was concentrated under reduced pressure. The residue was purified chromatographically. This gave tert-butyl 4-(4-ethynyl-1,3-thiazol-2-yl)piperidine-1-carboxylate (493 mg).

Workup

  1. extractionAfter aqueous work-up, the mixture was extracted with ethyl acetate
  2. dry with materialthe extracts were dried with sodium sulphate
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThe residue was purified chromatographically

Sources & evidence

ORD record
ord-c73e0e36ba5b47f18e1ba6317e3a937b
Source dataset
uspto-grants-2016_06
Patent number
US09357779B2

Reaction notes

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