Imidazole → tert-butyl N-(3-iodopropyl)carbamate

HRID 660516Notes

Reaction equation

HRID 660516 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[C:27]([O:31][C:32](=[O:38])[NH:33][CH2:34][CH2:35][CH2:36]O)([CH3:30])([CH3:29])[CH3:28]>C(Cl)Cl>[C:27]([O:31][C:32](=[O:38])[NH:33][CH2:34][CH2:35][CH2:36][I:25])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 11231463tert-butyl N-(3-iodopropyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of triphenylphosphine (28.5 g, 108.6 mmol) and imidazole (7.39 g, 108.6 mmol) in CH2Cl2 (400 mL) at RT, is added iodine (28.92 g, 113.95 mmol) portionwise. To this solution is added a solution of (3-hydroxypropyl)-carbamic acid tert-butyl ester (18.66 g, 106.49 mmol) (Synthesis 1990, 366) in CH2Cl2 (75 mL) dropwise and the mixture allowed to stir at RT for 14 h. The mixture is then filtered and the filtrate concentrated to a crude red oil, which is partitioned between ether and sat. sodium thiosulfate. The aqueous phase is extracted with ether. The combined organic layers are reduced to 200 mL and then filtered through a plug of silica, eluting with ether. Evaporation of solvent affords the title compound.

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationthe filtrate concentrated to a crude red oil, which
  3. customis partitioned between ether and sat. sodium thiosulfate
  4. extractionThe aqueous phase is extracted with ether
  5. filtrationfiltered through a plug of silica
  6. washeluting with ether
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-6e46ef1b7bac42e3ba897263bd78a931
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…