1-Pentyne → HCID 59657497, compound

HRID 494161Notes

Reaction equation

HRID 494161 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH3:5].C([Li])CCC.[CH2:11]([N:18]1[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH2:11]([N:18]1[CH2:23][CH2:22][C:21]([C:1]#[C:2][CH2:3][CH2:4][CH3:5])([OH:24])[CH2:20][CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 123091-PentyneHCID 192201-Benzyl-4-piperidoneHCID 178418339Butyllithium

Product 1

HCID 59657497HCID 59657497, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 5.47 g (80.3 mmol) of 1-pentyne in 65 mL THF at −78° C. was added 32.1 ml n-butyl lithium (80.3 mmol; 2.5M in hexanes). After the addition was complete the reaction mixture was warmed to 0° C. and a solution of 8.44 g (44.6 mmol) of 1-benzyl-4-piperidone and 40 mL of THF was added dropwise. The cooling bath was removed and the reaction mixture was stirred at ambient temperature. After 17 h, the reaction was quenched by addition of saturated ammonium chloride and diluted with EtOAc. The aqueous phase was extracted twice with EtOAc. The combined organic phases were washed with brine, dried over sodium sulfate and evaporated to afford a reddish-gold oil. The crude product was purified by flash chromatography on silica gel (EtOAc/hexane 1:1→65:35). The light gold oil was dried over sodium sulfate to afford 8.91 g (78%) of 1-benzyl-4-pentynyl-4-piperidinol: ms (ESI) [M+H]+=258.

Workup

  1. additionAfter the addition
  2. customThe cooling bath was removed
  3. customthe reaction was quenched by addition of saturated ammonium chloride
  4. additiondiluted with EtOAc
  5. extractionThe aqueous phase was extracted twice with EtOAc
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto afford a reddish-gold oil
  10. customThe crude product was purified by flash chromatography on silica gel (EtOAc/hexane 1:1→65:35)
  11. dry with materialThe light gold oil was dried over sodium sulfate

Sources & evidence

ORD record
ord-63aa5bd833914319a857d1616ee3a47a
Source dataset
uspto-grants-2009_05
Patent number
US07538122B2

Reaction notes

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