Imidazole → tert-Butyl 3-(2-iodoethyl)azetidine-1-carboxylate

HRID 1198503Notes

Reaction equation

HRID 1198503 reaction equation
[C:1]([N:8]1[CH2:11][CH:10]([CH:12](O)[CH3:13])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:39]I>CC#N>[C:1]([N:8]1[CH2:11][CH:10]([CH2:12][CH2:13][I:39])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 58348207Tert-butyl 3-(1-hydroxyethyl)azetidine-1-carboxylate

Product 1

HCID 19034125tert-Butyl 3-(2-iodoethyl)azetidine-1-carboxylateYield 83.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 133 (0.78 g, 3.8 mmol), PPh3 (1.1 g, 4.3 mmol), imidazole (0.40 g, 5.8 mmol), and CH3CN (20 mL) at 0° C. was treated with iodine (1.0 g, 4.3 mmol). After 15 min the cooling bath was removed and stirring continued for 5 h. The reaction mixture was then diluted with H2O and extracted with hexanes (5×25 mL then 4×50 mL). The combined extracts were dried (MgSO4) and concentrated. Flash chromatography (silica, 20% EtOAc/hexanes) gave 134 (0.99 g) as a colorless oil. Rf 0.44 (silica, 20% EtOAc/hexanes). 1H NMR (400 MHz, CDCl3) δ 4.04 (t, J=7 Hz, 2H), 3.57 (dd, 2H), 3.10 (t, 2H), 2.64 (m, 1H), 2.16 (q, 2H), 1.43 (s, 9H). ##STR59##

Workup

  1. customAfter 15 min the cooling bath was removed
  2. additionThe reaction mixture was then diluted with H2O
  3. extractionextracted with hexanes (5×25 mL
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a390cfaa258f442dbd10b2ff85bf3f04
Source dataset
uspto-grants-1994_01
Patent number
US05281585

Reaction notes

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