HCID 277278, compound → HCID 86627344, compound

HRID 1896006Notes

Reaction equation

HRID 1896006 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:11](P(=O)(OCC)OCC)[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:28]([N:35]1[CH2:40][CH2:39][C:38](=O)[CH2:37][CH2:36]1)([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>C1COCC1>[C:14]1(/[CH:13]=[CH:12]/[CH:11]=[C:38]2[CH2:39][CH2:40][N:35]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:36][CH2:37]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 277278HCID 277278, compoundHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 86627344HCID 86627344, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium bis(trimethylsilyl)amide (1M sol. in THF, 2.63 mL, 2.63 mmol) was added at −60° C. under nitrogen atmosphere to a solution of diethyl cinnamylphosphonate (0.629 mL, 2.64 mmol). After 15 min. under stirring at the same temperature, N-Boc-4-piperidone (500 mg, 2.51 mmol) dissolved in THF (5 ml) was added. Stirring and cooling was maintained for 30 min and, after 2 h, the reaction mixture was quenched with water and with EtOAc. The combined extracts were washed, dried over Na2SO4 and evaporated to dryness affording the title product (752 mg), that was used in the next step without further purification.

Workup

  1. additionwas added
  2. temperaturecooling
  3. temperaturewas maintained for 30 min and, after 2 h
  4. customthe reaction mixture was quenched with water and with EtOAc
  5. washThe combined extracts were washed
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-0843f03c3e0a4838a89f113f95555e7e
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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