Imidazole → Tert-butyl 3-iodoazetidine-1-carboxylate

HRID 1918974Notes

Reaction equation

HRID 1918974 reaction equation
O[CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.N1C=CN=C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[I:37]I.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[I:37][CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1

Participants

7

Reactant 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylateYield 93.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (25-3) (3.5 g, 0.02 mol) in toluene (200 mL) was treated with imidazole (4.08 g, 0.06 mol), PPh3 (0.6 g, 0.04 mol), and I2 (7.62 g, 0.03 mol). The mixture was heated at 100° C. for 1 h and cooled down to room temperature. It was then poured into saturated NaHCO3 solution (30 mL). Excess PPh3 was destroyed by addition of iodine until I2 coloration persisted in organic layer. The mixture was washed with 5% Na2SO3 solution, dried over Na2SO4, and evaporated in vacuo. The residue was purified on silica gel column to give 199a (5.31 g, 93%). MS: [M+H]+ 284.

Workup

  1. temperaturecooled down to room temperature
  2. customExcess PPh3 was destroyed by addition of iodine until I2 coloration
  3. washThe mixture was washed with 5% Na2SO3 solution
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo
  6. customThe residue was purified on silica gel column

Sources & evidence

ORD record
ord-06350117f5ac4cf687af3920837e2e57
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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