Imidazole → Tert-butyl 3-iodoazetidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10](O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:37]I.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([I:37])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Conditions
- Temperature
- 100 °C
Procedure
A solution of 3-hydroxy-azetidine-1-carboxylic acid tert-butyl ester (3.35 g, 19.34 mmol) in toluene (200 ml) was treated with imidazole (3.95 g, 58.01 mmol), triphenyl-phosphine (10.14 g, 38.65 mmol) and I2 (7.36 g, 28.99 mmol). The mixture was heated at 100° C. for 1 h, cooled down to room temperature and subsequently poured into a saturated aqueous solution of NaHCO3 (30 ml). Excess triphenylphosphine was destroyed by addition of iodine until I2 coloration persisted in organic layer. The latter was washed with an aqueous solution of Na2S2O3 (5% strength), dried over Na2SO4, filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (heptane:EtOAc, 2:1) provides the title compound (5.19 g, 95%) as a light yellow oil.
Workup
- temperaturecooled down to room temperature
- customExcess triphenylphosphine was destroyed by addition of iodine until I2 coloration
- washThe latter was washed with an aqueous solution of Na2S2O3 (5% strength)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customPurification of the residue by flash column chromatography (heptane:EtOAc, 2:1)
Sources & evidence
- ORD record
- ord-c745c8214de84ad2820773a12142448e
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242102B2
Reaction notes
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