Diiodomethane → HCID 11586840, compound

HRID 2253037Notes

Reaction equation

HRID 2253037 reaction equation
[CH2:1]([Zn]CC)C.FC(F)(F)C(O)=O.ICI.C(OC([N:23]1[CH2:28][CH2:27][O:26][C@H:25]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([CH:38]=[CH2:39])[CH:31]=2)[CH2:24]1)=O)(C)(C)C>ClCCl>[CH:38]1([C:32]2[CH:31]=[C:30]([CH:35]=[CH:34][C:33]=2[O:36][CH3:37])[CH2:29][C@H:25]2[O:26][CH2:27][CH2:28][NH:23][CH2:24]2)[CH2:39][CH2:1]1

Participants

6

Reactant 4

HCID 6346DiiodomethaneHCID 6422Trifluoroacetic acidHCID 67073058HCID 67073058, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 11586840HCID 11586840, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

The solution of 0.98 mL (1.1 mmol; 1.1M solution in toluene) diethyl zinc in 2 mL dichloromethane was cooled down to 0° C. Then 0.8 mL trifluoroacetic acid in 2 mL dichloromethane and after 25 min. a solution of 0.29 g diiodomethane in 2 mL dichloromethane was added. After another 20 min. 0.18 g (0.54 mmol) (R)-2-(4-methoxy-3-vinyl-benzyl)-morpholine-4-carboxylic acid tert-butyl ester dissolved in 2 mL dichloromethane was added. The ice bath was removed and after 45 min. stirring at room temperature the reaction mixture was poured on 1M hydrochloric acid and extracted three times with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed using MPLC and dichloromethane:methanol:ammonia (9:1:0.1 v/v) as eluant to give the compound as a light brown oil (26%).

Workup

  1. additionwas added
  2. customThe ice bath was removed and after 45 min.
  3. additionwas poured on 1M hydrochloric acid
  4. extractionextracted three times with dichloromethane
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was chromatographed

Sources & evidence

ORD record
ord-d3d8647b15ca4323b7f654a4451bd2d5
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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