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

HRID 1602648Notes

Reaction equation

HRID 1602648 reaction equation
[CH2:1]([N:8]1[C@H:12]([CH2:13]O)[CH2:11][CH2:10][C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:40]I>CCOCC.C(#N)C>[CH2:1]([N:8]1[C@H:12]([CH2:13][I:40])[CH2:11][CH2:10][C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 10442943(S)-1-Benzyl-5-hydroxymethyl-2-pyrrolidinone

Product 1

HCID 10425818(S)-5-iodomethyl-1-(phenylmethyl)-2-pyrrolidinone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 13-1 (18.5 g, 90.1 mmol), triphenylphosphine (40.1 g, 153 mmol), and imidazole (11.03 g, 162 mmol) in 225 mnL of acetonitrile and 150 mL of ether at 0° C. was added iodine (34.3 g, 135 mmol) in 5 portions over 5 minutes. After 10 minutes, the reaction was heated to 50° C., and a stream of argon passed over the reaction to purge the evaporating ether. After an additional 30 minutes, the mixture was diluted with ether, the organic layer washed with NaHCO3 (sat.) and brine, dried over K2CO3, and the solvent evaporated. Flash chromatography of the residue (silica, 7-15% EtOAc/CHCl3) gave 13-2 as a yellow oil.

Workup

  1. customa stream of argon passed over the reaction
  2. customto purge the evaporating ether
  3. waitAfter an additional 30 minutes
  4. additionthe mixture was diluted with ether
  5. washthe organic layer washed with NaHCO3 (sat.) and brine
  6. dry with materialdried over K2CO3
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-ade771d594714a41b90c20ba94b611b2
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

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