Imidazole → tert-Butyl (4-iodobutyl)carbamate

HRID 660608Notes

Reaction equation

HRID 660608 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[I:20]I.N1C=CN=C1.[C:27]([O:31][C:32](=[O:39])[NH:33][CH2:34][CH2:35][CH2:36][CH2:37]O)([CH3:30])([CH3:29])[CH3:28]>C(Cl)Cl>[C:27]([O:31][C:32](=[O:39])[NH:33][CH2:34][CH2:35][CH2:36][CH2:37][I:20])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 545141tert-Butyl N-(4-hydroxybutyl)carbamate

Product 1

HCID 53439149tert-Butyl (4-iodobutyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of PPh3-resin (16.4 g, 21.1 mmol) in methylene chloride (150 mL) at 0° C. is added iodine (5.4 g, 21.2 mmol) and imidazole (1.66 g, 24.4 mmol) then stirring is continued at 0° C. for 45 min. To this is added (4-hydroxybutyl)-carbamic acid tert-butyl ester (2.0 g, 10.6 mmol) and the suspension is refluxed for 2 h. The suspension is filtered and the organic layer is washed with a saturated sodium bisulfite solution, water and brine, and dried over sodium sulfate. The solvent is removed under reduced pressure to afford the title compound as pale yellow liquid: 1H NMR (CDCl3) δ 4.51 (s, 1H), 3.21-3.17 (t, J=6.82 Hz, 2H), 3.16-3.11 (q, J=6.82 Hz, 2H), 1.88-1.81 (m, 2H), 1.62-1.55 (m, 2H), 1.43 (s, 9H).

Workup

  1. temperaturethe suspension is refluxed for 2 h
  2. filtrationThe suspension is filtered
  3. washthe organic layer is washed with a saturated sodium bisulfite solution, water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-d9fc2c6fcfc04e36a7ce5ce87bd6061d
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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