Imidazole → Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

HRID 2095408Notes

Reaction equation

HRID 2095408 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15]O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:41]I>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][I:41])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Product 1

HCID 9974426Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-(2-hydroxyethyl)piperidine (458 mg, 2.0 mmol), Ph3P (785 mg, 3.0 mmol, 1.5 equiv.) and imidazole (204 mg, 3.0 mmol, 1.5 equiv.) in toluene (10 mL) was added I2 (761 mg, 3.0 mmol, 1.5 equiv.) at 0° C. The mixture was allowed to stand at room temperature overnight, before it was quenched with saturated Na2S2O3 solution. The product was extracted into CH2Cl2, and the organic layer was washed with brine and dried over Na2SO4. After concentration, the residue was purified by CC (SiO2, hexane/EtOAc 8:1, then 4:1). After removal of the solvents, 1-(tert-butoxycarbonyl)-4-(2-iodoethyl)piperidine (560 mg, 83%) was obtained as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 4.09 (br, 2H), 3.21 (t, 2H, J=7.2 Hz), 2.70 (t, 2H, J=12.0 Hz), 1.77 (q, 2H, J=7.2 Hz), 1.65 (d, 2H, J=12.8 Hz), 1.56 (m, 1H), 1.45 (s, 9H), 1.11 (m, 2H).

Workup

  1. customwas quenched with saturated Na2S2O3 solution
  2. extractionThe product was extracted into CH2Cl2
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customthe residue was purified by CC (SiO2, hexane/EtOAc 8:1
  7. customAfter removal of the solvents

Sources & evidence

ORD record
ord-18f818283a6e40b883323117b3724616
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

Loading…