Dichloromethane → HCID 19597325, compound

HRID 611791Notes

Reaction equation

HRID 611791 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].CC([N-]C(C)C)C.O[CH2:23][CH2:24][CH2:25][C:26]1(CCC([O-])=O)[CH2:30][N:29]([C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:28]=[N:27]1.C([Li])CCC.S(OS(C(F)(F)F)(=O)=O)(C(F)(F)F)(=O)=O.[Li+].CC([N-]C(C)C)C.C1(N2CCCCC2=O)C=CC=CC=1.C(Cl)[Cl:97]>C1COCC1>[ClH:97].[C:44]1([C:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:29]2[CH:30]=[C:26]([CH2:25][CH2:24][CH2:23][CH:9]3[CH2:10][CH2:11][CH2:12][N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:8]3=[O:13])[N:27]=[CH:28]2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

9

Reactant 7

HCID 6344DichloromethaneHCID 67749Trifluoromethanesulfonic anhydrideHCID 5717601-phenylpiperidin-2-oneHCID 2724682Lithium diisopropylamideHCID 86754951HCID 86754951, compoundHCID 86754952HCID 86754952, compoundHCID 178418339Butyllithium

Product 1

HCID 19597325HCID 19597325, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-phenyl-2-piperidinone from Step F in THF is added to a solution of one equivalent of LDA in THF at -78° C., and stirred for 30 min. A solution of 4-(3-hydroxy-1-propyl)-3-(1-triphenylmethyl-4--imidazolyl)propionate in methylene chloride is cooled to -78° C. under nitrogen. One equivalent of n-butyl lithium followed by one equivalent of triflic anhydride is added, the reaction stirred for 10 min, then added to the LDA/1-phenyl-2-piperidinone solution. The reaction is warmed to room temperature, and quenched with saturated ammonium chloride. The reaction is then partitioned between ethyl acetate and saturated brine. The organic phase is dried over magnesium sulfate, filtered and concentrated. The title compound is isolated by chromatography on silica gel.

Workup

  1. additionis added
  2. stirringthe reaction stirred for 10 min
  3. customquenched with saturated ammonium chloride
  4. customThe reaction is then partitioned between ethyl acetate and saturated brine
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3ff37114aab5401299f0f41dcaff05d9
Source dataset
uspto-grants-1999_12
Patent number
US06001835

Reaction notes

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