HCID 58237942, compound → HCID 67104684, compound

HRID 1192935Notes

Reaction equation

HRID 1192935 reaction equation
[Li][CH2:2]CCC.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]([N:15]2[CH2:20][CH2:19][C@:18]([CH2:27][C:28](=O)[CH3:29])([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][C:16]2=[O:31])[CH3:14])=[CH:9][CH:8]=1>C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br-].C1COCC1>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C@@H:13]([N:15]2[CH2:20][CH2:19][C@:18]([CH2:27][C:28]([CH3:2])=[CH2:29])([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:17][C:16]2=[O:31])[CH3:14])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 58237942HCID 58237942, compoundHCID 178418339Butyllithium

Product 1

HCID 67104684HCID 67104684, compoundYield 60.6%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of CH3PPh3Br (863.9 mg 2.42 mmol) in THF (8 mL) was added n-BuLi (0.678 ml, 1.69 mmol) at −78° C. under N2. The mixture was stirred at rt for 1 h, a solution of (R)-1-((S)-1-(4-bromophenyl)ethyl)-4-(2-oxopropyl)-4-phenylpiperidin-2-one (100 mg 0.24 mmol) in THF (5 mL) was added, and the mixture was stirred at reflux overnight. The reaction was quenched by satd aq NH4Cl and extracted with EtOAc. The combined organic phase was dried and concentrated to give the crude product, which was purified by preparative TLC to give (S)-1-((S)-1-(4-bromophenyl)ethyl)-4-(2-methylallyl)-4-phenylpiperidin-2-one (60 mg, 60%).

Workup

  1. stirringthe mixture was stirred
  2. temperatureat reflux overnight
  3. customThe reaction was quenched by satd aq NH4Cl
  4. extractionextracted with EtOAc
  5. customThe combined organic phase was dried
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-2b1277ab3bd44abfbc707eb32c5a5814
Source dataset
uspto-grants-2014_03
Patent number
US08680281B2

Reaction notes

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