Diiodomethane → HCID 69759930, compound

HRID 1359356Notes

Reaction equation

HRID 1359356 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][C@@H:17]([O:19][CH:20]=[CH2:21])[C@H:16]([O:22][CH2:23][O:24][CH3:25])[CH2:15]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH2:27]I.C([Zn]CC)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1.CCCCCC>[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][C@@H:17]([O:19][CH:20]3[CH2:27][CH2:21]3)[C@H:16]([O:22][CH2:23][O:24][CH3:25])[CH2:15]2)[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 69758150HCID 69758150, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 69759930HCID 69759930, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 229 mg of 2-benzyl-6-[(3R,4R)-3-methoxymethyloxy-4-vinyloxypyrrolidine-1-yl]pyridine, 217 μl of diiodomethane, 1.35 ml of hexane solution containing 1.0 mol of diethylzinc and 3 ml of toluene was stirred at 80° C. for 3 hours. Ammonium chloride was added to the reaction solution, and the mixture was washed with brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 15% ethyl acetate/hexane, to give 47.8 mg of the target compound.

Workup

  1. washthe mixture was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-19e83206e9de40ab970094aab84ecb11
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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