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

HRID 549946Notes

Reaction equation

HRID 549946 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) is dissolved in methanol, and potassium carbonate (839 mg) and dimethyl 1-diazo-2-oxopropylphosphonate (786 mg) are added. The mixture is stirred at room temperature for 3 hours. After aqueous work-up, the mixture is extracted with ethyl acetate and the extracts are dried with sodium sulphate and concentrated under reduced pressure. The residue is purified chromatographically. This gives tert-butyl 4-(4-ethynyl-1,3-thiazol-2-yl)piperidine-1-carboxylate (493 mg).

Workup

  1. extractionAfter aqueous work-up, the mixture is extracted with ethyl acetate
  2. dry with materialthe extracts are dried with sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified chromatographically

Sources & evidence

ORD record
ord-eb59adcd898b47b4a81f9cc68aa5b946
Source dataset
uspto-grants-2011_05
Patent number
US07943774B2

Reaction notes

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