N-[3-(4-Fluorophenyl)-3-oxopropyl]pipecolic acid methyl ester → Methyl pipecolinate

HRID 1744896Notes

Reaction equation

HRID 1744896 reaction equation
ClC1C=CC([Mg]I)=CC=1.[CH3:10][O:11][C:12](=[O:30])[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][N:14]1CCC(C1C=CC(F)=CC=1)=O>C(OCC)C>[CH3:10][O:11][C:12](=[O:30])[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][NH:14]1

Participants

4

Reactant 2

HCID 53681476N-[3-(4-Fluorophenyl)-3-oxopropyl]pipecolic acid methyl esterHCID 178478194HCID 178478194, compound

Product 1

HCID 3463753Methyl pipecolinateYield 4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

7 ml (2 mmol) of 0.28 M solution of 4-chlorophenylmagnesium iodide in diethyl ether [prepared from 1-chloro-4-iodobenzene (Aldrich) and magnesium] was added dropwise to an ice-cooled solution of 0.605 g (2 mmol) N-[3-4-fluorophenyl)-3-oxopropyl]pipecolic acid methyl ester (from Step 1) in 12 ml anhydrous diethyl ether with stirring under nitrogen. The mixture was stirred at room temperature for 16 hours, poured onto crushed ice and extracted with dichloromethane. The combined organic extracts were washed with brine, concentrated and the residue purified by preparative silica gel TLC with 25% ethyl acetate in hexanes to give 0.037 g (yield 4.5%) N-[3-4-chlorophenyl)-3-(4-fluorophenyl)-3-hydroxypropyl]pipecolic acid methyl ester (Compound B30).

Workup

  1. stirringThe mixture was stirred at room temperature for 16 hours
  2. additionpoured
  3. customonto crushed ice
  4. extractionextracted with dichloromethane
  5. washThe combined organic extracts were washed with brine
  6. concentrationconcentrated
  7. customthe residue purified by preparative silica gel TLC with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-cb1652d8c91448c0950f5a32582c9460
Source dataset
uspto-grants-2006_03
Patent number
US07019024B2

Reaction notes

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