HCID 18723461, compound → HCID 18335085, compound

HRID 842225Notes

Reaction equation

HRID 842225 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. 1H NMR (CDCl3) δ (key peaks) 7.88-7.89 (m, 3H), 7.45-7.57 (m, 4H), 7.13-7.19 (m, 2H), 6.94-6.99 (m, 2H), 1.31 and 1.08 (s, 3H), 1.25 and 0.91 (s, 3H); Mass Spectrum (ESI) m/e=475 (M+1).

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-a2c393050c2c42368bc22caa3555f156
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

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