Imidazole → 1-Benzyl-4-iodomethyl-pyrrolidin-2-one

HRID 1374177Notes

Reaction equation

HRID 1374177 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([CH2:13]O)[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>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][CH:11]([CH2:13][I:40])[CH2:10][C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 1788241-Benzyl-4-(hydroxymethyl)pyrrolidin-2-one

Product 1

HCID 128272761-Benzyl-4-iodomethyl-pyrrolidin-2-oneYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To alcohol lactam 74 (11.18 g, 0.056 mol) in 210 mL toluene was added in turn, triphenylphosphine (20.0 g, 0.076 mol), imidazole (10.8 g, 0.159 mol), and iodine (19.0 g, 0.075 mol). After stirring the suspension for 1.5 hours, the supernatant was poured into another flask. The sticky yellow residue was washed twice with ether and the solutions were combined. The solvent was evaporated and the residue was chromatographed on silica, eluting with 1:1 acetone/hexane to give 7.92 g, 46% of the iodolactam 75 as yellow oil. 1H NMR (CDCl3) δ 7.25 (m, 5H), 4.38 (d, 1H, J=14.6), 4.46 (d, 1H, J=14.6), 3.38 (dd, 1H, J=7.8 and 2.2), 3.20 (dd, 1H, J=5.6 and 4.4), 3.12 (dd, 1H, J=7.3 and 2.4), 2.96 (dd, 1H, J=5.8 and 4.4), 2.60 (m, 2H), 2.22 (dd, 1H, J=10.5 and 9.7). MS, m/z (relative intensity): 224 [M−H−Bn, 94%], 317 [M+2H, 64%]. IR 3027, 2917, 1688, 1438, 1267, and 701 cm−1.

Workup

  1. additionthe supernatant was poured into another flask
  2. washThe sticky yellow residue was washed twice with ether
  3. customThe solvent was evaporated
  4. customthe residue was chromatographed on silica
  5. washeluting with 1:1 acetone/hexane

Sources & evidence

ORD record
ord-efd0415ec7c24c5e897f536d0195e9d3
Source dataset
uspto-grants-2007_01
Patent number
US07164034B2

Reaction notes

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