Imidazole → HCID 86614566, compound

HRID 1672384Notes

Reaction equation

HRID 1672384 reaction equation
[CH2:1]([N:8]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:9][C:10]1([CH2:13]O)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.CCOCC.C(#N)C.[I:52]I>>[CH2:1]([N:8]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:9][C:10]1([CH2:13][I:52])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 6

HCID 795ImidazoleHCID 807IodineHCID 3283Diethyl EtherHCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 86614564HCID 86614564, compound

Product 1

HCID 86614566HCID 86614566, compoundYield 63.8%

Conditions

Temperature
0 °C

Procedure

To a stirred solution of methyl (benzyl{[1-(hydroxymethyl)cyclopropyl]methyl}-amino)acetate (1.1 g, 0.0042 mol), triphenylphosphine (2.74 g, 0.0104 mol) and 1H-imidazole (0.711 g, 0.0104 mol) in ether (30.0 mL, 0.286 mol) and ACN (10.0 mL, 0.192 mol) at 0° C. was added iodine (2.12 g, 0.00835 mol). The resulting yellow suspension was stirred at 0° C. for 50 min. The reaction was quenched by the addition of 10% aqueous Na2S2O3 (30 ml) and saturated aqueous NaHCO3 (30 mL). The product was extracted with EtOAc (2×) and the combined organic extracts were washed with brine, then dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by Combiflash chromatography eluting with 0-15% EtOAc/hexanes to afford the desired product (1.0 g). LC/MS: 374.1 (M+1H)+.

Workup

  1. customThe reaction was quenched by the addition of 10% aqueous Na2S2O3 (30 ml) and saturated aqueous NaHCO3 (30 mL)
  2. extractionThe product was extracted with EtOAc (2×)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by Combiflash chromatography
  8. washeluting with 0-15% EtOAc/hexanes

Sources & evidence

ORD record
ord-80d8140b53704cf09fe6dc907c30b85b
Source dataset
uspto-grants-2011_08
Patent number
US07998959B2

Reaction notes

Loading…