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
7
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), triphenylphosphine (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 next poured into saturated aqueous NaHCO3 (30 ml). Excess triphenylphosphine was destroyed by addition of iodine until I2 coloration persisted in organic layer. The latter was washed with 5% aqueous Na2S2O3, dried over Na2SO4 and evaporated. Purification of the crude product by flash column chromatography (heptane:ethyl acetate, 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 5% aqueous Na2S2O3
- dry with materialdried over Na2SO4
- customevaporated
- customPurification of the crude product by flash column chromatography (heptane:ethyl acetate, 2:1)
Sources & evidence
- ORD record
- ord-17bbad8de2bd41c5802e9d8167e539e0
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470810B2
Reaction notes
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