tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 21912813, compound

HRID 1245575Notes

Reaction equation

HRID 1245575 reaction equation
[CH2:1]([N:3]1[C:11](Br)=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]2)=[N:4]1)[CH3:2].[Li]C(C)(C)C.[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>C1COCC1>[C:28]([O:27][C:25]([N:22]1[CH2:23][CH2:24][C:19]([OH:18])([C:11]2[N:3]([CH2:1][CH3:2])[N:4]=[C:5]3[C:10]=2[CH:9]=[CH:8][CH:7]=[CH:6]3)[CH2:20][CH2:21]1)=[O:26])([CH3:31])([CH3:29])[CH3:30]

Participants

5

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 21912705HCID 21912705, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 21912813HCID 21912813, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-ethyl-3-bromoindazole (3.4 g, 15.18 mmol) in THF (30 mL) was added t-BuLi (1.7 M in pentane, 10.72 mL, 18.22 mmol) dropwise at −78° C. After stirring at −78° C. for 20 min., was added tert-butyl 4-oxo-1-piperidinecarboxylate (3.03 g, 15.18 mmol) in THF (10 mL) dropwise at −78° C. The mixture was stirred at −78° C. for 10 min. and at rt for 18 h. After the reaction was quenched with aq. NH4Cl, the mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (3×). The combined organic phases were washed with brine, and dried over anhydrous magnesium sulfate. Concentration followed by purification by flash chromatography (hexanes:ethyl acetate=4:1, then 1:1) to give the title compound as a foamy solid.

Workup

  1. stirringThe mixture was stirred at −78° C. for 10 min. and at rt for 18 h
  2. customAfter the reaction was quenched with aq. NH4Cl
  3. customthe mixture was partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationConcentration
  8. customfollowed by purification by flash chromatography (hexanes

Sources & evidence

ORD record
ord-e684956f7abd4a7c94b041cf7db4a102
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

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