Water → HCID 58550888, compound

HRID 1908039Notes

Reaction equation

HRID 1908039 reaction equation
Cl[C:2]1[C:7]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[O:18]=[C:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1.O>C1COCC1>[N:9]1[N:8]2[C:7]3[CH:6]=[CH:5][CH:4]=[N:3][C:2]=3[O:18][C:19]3([CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]3)[C:12]2=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 58551572HCID 58551572, compoundHCID 178418339Butyllithium

Product 1

HCID 58550888HCID 58550888, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-chloro-3-pyrazol-1-yl-pyridine (338 mg, 1.88 mmol) in THF (3.4 mL) at −78° C. was added butyllithium (979 μL of 2.5 M, 2.45 mmol) dropwise over 5 minutes. The reaction mixture was then stirred at the temperature for 15 minutes before the addition of tert-butyl 4-oxopiperidine-1-carboxylate (562.5 mg, 2.82 mmol). The reaction was allowed to come to 25° C., then heated at 70° C. for 4 hours. The reaction mixture was poured into water, and extracted with EtOAc (3×). The organics were combined, washed with brine, dried (Na2SO4) and evaporated to dryness to yield a crude mixture that was purified by column chromatography (5 to 30% EtOAC in hexanes) to give the title product (35 mg, 5%) that was used in the next step without further purification. ESI-MS m/z calc. 342.2. found 343.3 (M+1)+. Retention time: 1.46 minutes (3 min run).

Workup

  1. customto come to 25° C.
  2. extractionextracted with EtOAc (3×)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customto yield a crude mixture that
  7. customwas purified by column chromatography (5 to 30% EtOAC in hexanes)

Sources & evidence

ORD record
ord-92aa021b45844a7da5718952fe932fdd
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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