Acetone → (S)-5-iodomethyl-1-(phenylmethyl)-2-pyrrolidinone

HRID 2050938Notes

Reaction equation

HRID 2050938 reaction equation
CC1C=CC(S([CH2:11][C@H:12]2[N:16]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15](=[O:24])[CH2:14][CH2:13]2)(=O)=O)=CC=1.[I-:25].[Na+].CC(C)=O>C1CCCCC1>[I:25][CH2:11][C@H:12]1[N:16]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15](=[O:24])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 53977132(S)-5-[[(4-methylphenyl)sulfonyl]methyl]-1-(phenylmethyl)-2-pyrrolidinone

Product 1

HCID 10425818(S)-5-iodomethyl-1-(phenylmethyl)-2-pyrrolidinoneYield 92%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of (S)-5-[[(4-methylphenyl)sulfonyl]methyl]-1-(phenylmethyl)-2-pyrrolidinone (244.5 g, 0.68 mol), sodium iodide (305 g, 2.03 mol), and 3 L of acetone was refluxed and stirred overnight. The suspension was cooled to 10° C. and was filtered. The salts were rinsed with three 250-mL portions of acetone, and the acetone washes and filtrate were concentrated on a rotary evaporator to a thick slurry. Methylene chloride (1.5 L) was added and the white precipitate was filtered off and washed with methylene chloride. The filtrate was dried over magnesium sulfate (MgSO4), filtered through a pad of silica gel, and concentrated on a rotary evaporator to give 196.8 g (92% yield) of (S)-5-iodomethyl-1-(phenylmethyl)-2-pyrrolidinone as an off-white solid, mp 92°-94° C. (cyclohexane). 1 h NMR (CDCl3) δ 1.7-2.75 (m, 4 H, CH2), 3.18-3.28 (m, 2 H, CH2I), 3.42 (m, 1 H, NCH), 3.98 and 4.05 (AB, 2 H, Jgem =15 Hz, CH2Ph), 7.20 (m, 5 H, phenyl). [α]25D =+12.11 (c 0.35, methanol). Anal. Calcd for C12H14NOI: C, 45.73; H, 4.48; N, 4.44. Found: C, 45.58; H, 4.35; N, 4.22.

Workup

  1. temperaturewas refluxed
  2. filtrationwas filtered
  3. washThe salts were rinsed with three 250-mL portions of acetone
  4. concentrationand filtrate were concentrated on a rotary evaporator to a thick slurry
  5. additionMethylene chloride (1.5 L) was added
  6. filtrationthe white precipitate was filtered off
  7. washwashed with methylene chloride
  8. dry with materialThe filtrate was dried over magnesium sulfate (MgSO4)
  9. filtrationfiltered through a pad of silica gel
  10. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-9ab23c2caf564032bf604dc79b48ecf4
Source dataset
uspto-grants-1991_05
Patent number
US05015653

Reaction notes

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