tert-Butyl 4-oxopiperidine-1-carboxylate → HCID 21268342, compound

HRID 1457004Notes

Reaction equation

HRID 1457004 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.C([Li])CCC.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:26]3([OH:29])[CH2:25][CH2:24][N:23]([C:21]([O:20][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:22])[CH2:28][CH2:27]3)=[CH:7][C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 113097545-Chlorobenzo(b)thiopheneHCID 178418339Butyllithium

Product 1

HCID 21268342HCID 21268342, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 0.60 gm (3.56 mMol) 5-chlorobenzothiophene 1.55 mL in 20 mL freshly distilled tetrahydrofuran was cooled to -78° C. under a nitrogen atmosphere. To this was then added a solution of 2.94 mL (3.56 mMol) n-butyllithium and the reaction mixture was stirred at -78° C. for 1 hour. To the resulting anion solution was added dropwise a solution of 0.779 gm (3.91 mMol) 1-tert-butoxycarbonyl-4-piperidone and then the reaction mixture was allowed to warm to 0° C. The reaction mixture was then quenched with saturated aqueous sodium bicarbonate, diluted with 1:1 hexanes:diethyl ether and the phases separated. The organic phase was washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to flash silica chromatography, eluting with toluene containing 10% ethyl acetate. Fractions shown to contain product were combined and concentrated under reduced pressure to give 1.09 gm of the desired compound as a colorless foam contaminated with 20% 1-tert-butoxycarbonyl-4-piperidone.

Workup

  1. temperatureto warm to 0° C
  2. customThe reaction mixture was then quenched with saturated aqueous sodium bicarbonate
  3. additiondiluted with 1:1 hexanes
  4. customdiethyl ether and the phases separated
  5. washThe organic phase was washed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluting with toluene containing 10% ethyl acetate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e43ef2f8a9f48bf90828cb0218838f5
Source dataset
uspto-grants-1998_12
Patent number
US05846982

Reaction notes

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