HCID 18723461, compound → HCID 18335085, compound

HRID 2296829Notes

Reaction equation

HRID 2296829 reaction equation
[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([C:18](=[O:20])[CH3:19])[CH:15]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:35][Mg+].[Br-]>C1COCC1>[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([C:18]([OH:20])([CH3:35])[CH3:19])[CH:15]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)[CH2:24][CH2:23]3)[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 18723461HCID 18723461, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 18335085HCID 18335085, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.03 g (0.065 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-acetylpyrrolidine in 20 mL of THF at rt was added 0.19 mL (0.195 mmol) of MeMgBr (1M in THF) and the reaction mixture was stirred for 30 min. The reaction mixture was partitioned between CH2Cl2 and NaHCO3. The organic fraction was filtered through a thin pad of Celite and the filtrate was concentrated. The residue was purified by chromatography (silica, MeOH:CH2Cl2, 2:98) to give the title compound.

Workup

  1. customThe reaction mixture was partitioned between CH2Cl2 and NaHCO3
  2. filtrationThe organic fraction was filtered through a thin pad of Celite
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by chromatography (silica, MeOH:CH2Cl2, 2:98)

Sources & evidence

ORD record
ord-6b4438153a7d4630998019401b9fc158
Source dataset
uspto-grants-2002_12
Patent number
US06489354B1

Reaction notes

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