Isopropyl iodide → HCID 22236567, compound

HRID 1743755Notes

Reaction equation

HRID 1743755 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:16]=[CH:17][C:18](=[O:21])[NH:19][CH:20]=2)[CH2:10]1.C([O-])([O-])=O.[Na+].[Na+].[CH:28](I)([CH3:30])[CH3:29]>C1(C)C=CC=CC=1>[CH:28]([N:19]1[CH:20]=[C:15]([CH2:14][N:11]2[CH2:12][CH2:13][CH:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:10]2)[CH:16]=[CH:17][C:18]1=[O:21])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 6362Isopropyl iodide2×HCID 10340Sodium CarbonateHCID 22236563HCID 22236563, compound

Product 1

HCID 22236567HCID 22236567, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9.75 g of (+)-5-[3-(2-methoxyphenyl)pyrrolidin-1-ylmethyl]-1H-pyridin-2-one (example 2) are dissolved in 170 ml of toluene. 14.2 g of Na2CO3, followed by 6.9 ml of isopropyl-iodide are added to the solution which is stirred at 100° overnight. Subsequently, another 3.4 g of isopropyliodide are added and stirring continued for additional 17 hours. The reaction solution is extracted with water and the combined organic phases dried and evaporated resulting in an oily residue which is purified by flash chromatography on silica gel using CH2Cl2/MeOH/conc. aqueous NH4OH 95/4.5/0.5 as solvent system which provides (+)-1-Isopropyl-5-[3-(2-methoxyphenyl)pyrrolidin-1-ylmethyl]-1H-pyridin-2-one {[αD25]=+19.7° (c=1.0, EtOH); MS (Cl): MH+=327; NMR (DMSO, 120°): 1.3 (6H, d), 1.95 (1H, m), 2.3 (1H, m), 2.7-3.4 (4H, m), 3.6-3.8 (3H, m), 3.8 (3H, s), 5.0 (1H, q), 6.35 (1H, d) 6.9-7.0 (2H, m), 7.2 (1H, t), 7.3 (1H, m), 7.4 (1H, m), 7.6 (1H, m)} and (+)-2-Isopropoxy-5-[3-2-methoxyphenyl)pyrrolidin-1-ylmethyl]-1H-pyridine {[αD25]=+22.8° (c=1.0, EtOH); MS (EI): M+=326; NMR (DMSO): 1.3 (6H, d), 1.75 (1H, m), 2.15 (1H, m), 2.4 (1H, t), 2.65 (2H, m), 2.8 (1H, t), 3.5-3.65 (3H, m), 3.75 (3H, s), 5.2 (1H, m), 6.7 (1H, d), 6.85-6.95 (2H, m), 7.15 (1H, t), 7.3 (1H, d), 7.6 (1H, m), 8.05 (1H, s)}

Workup

  1. additionare added to the solution which
  2. stirringstirring
  3. waitcontinued for additional 17 hours
  4. extractionThe reaction solution is extracted with water
  5. customthe combined organic phases dried
  6. customevaporated
  7. customresulting in an oily residue which
  8. customis purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-092b6f58691c41deb671d733816ae1d5
Source dataset
uspto-grants-2006_03
Patent number
US07012085B2

Reaction notes

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