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

HRID 1506590Notes

Reaction equation

HRID 1506590 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-oxopropylphosphonate (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-a68ccc75e5dc4b298a0d376c0febb595
Source dataset
uspto-grants-2015_12
Patent number
US09220266B2

Reaction notes

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