Allyl iodide → HCID 21341534, compound

HRID 2185516Notes

Reaction equation

HRID 2185516 reaction equation
[CH2:1](I)[CH:2]=[CH2:3].[CH2:5]([O:7][C:8](=[O:22])[C@@H:9]1[CH2:13][C@@H:12]([OH:14])[CH2:11][N:10]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH3:6]>CN(C)C=O.[Ag]=O>[CH2:5]([O:7][C:8](=[O:22])[C@@H:9]1[CH2:13][C@@H:12]([O:14][CH2:3][CH:2]=[CH2:1])[CH2:11][N:10]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH3:6]

Participants

5

Reactant 2

HCID 11166Allyl iodideHCID 12709318HCID 12709318, compound

Product 1

HCID 21341534HCID 21341534, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Freshly prepared silver oxide (5.32 g, 3 eq.) and allyl iodide (15 mL, 4 eq.) were added to a solution of N-(tert-butoxycarbonyl)-trans-4-hydroxy-L-proline ethyl ester (2.2 g, 7.71 mmol) in dimethylformamide (15 mL) under a nitrogen atmosphere. The reaction mixture was stirred at 25° C. for 12 hours, then at 55° C. for 5 hours. The reaction mixture was filtered, poured into ethyl acetate, washed twice with water, once with brine, dried (Na2SO4), concentrated and purifed by flash chromatography (20% ethyl acetate/hexane) to give the title compound (2.18 g, 94%) as a clear oil. 1H NMR (300 MHz, CDCl3) δ 1.38 (m, 3H), 1.48, 1.54 (2s, 9H), 2.17 (m, 1H), 2.23 (m, 1H), 3.58 (bd, J=12.4 Hz, 0.5H), 3.70 (m, 1.5H), 4.05 (m, 2H), 4.22 (m, 3H), 4.43 (m, 1H), 5.29 (dd, J=10.1; 0.7 Hz, 1H), 5.39 (dd, J=17.6; 0.6 Hz, 1H) and 5.99 (m, 1H).

Workup

  1. waitat 55° C. for 5 hours
  2. filtrationThe reaction mixture was filtered
  3. additionpoured into ethyl acetate
  4. washwashed twice with water, once with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f3890d7cacfe4268a361bcef1de5c388
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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