1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-Benzyl-5-bromo-2-[(3r,4r)-3,4-dihydroxypyrrolidine-1-yl]pyridine

HRID 1359396Notes

Reaction equation

HRID 1359396 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([Br:20])=[CH:9][N:8]=1)(=O)=O.C(O)(=O)C.[OH:27][C@H:28]1[C@H:32]([OH:33])[CH2:31][NH:30][CH2:29]1.C1CCN2C(=NCCC2)CC1>O1CCCC1>[CH2:13]([C:11]1[C:10]([Br:20])=[CH:9][N:8]=[C:7]([N:30]2[CH2:31][C@@H:32]([OH:33])[C@H:28]([OH:27])[CH2:29]2)[CH:12]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 181821814-Benzyl-5-bromo-2-pyridyl trifluoromethanesulfonateHCID 69363142(3R,4R)-3,4-dihydroxypyrrolidine acetate

Product 1

HCID 697586594-Benzyl-5-bromo-2-[(3r,4r)-3,4-dihydroxypyrrolidine-1-yl]pyridineYield 47.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4.0 g of 4-benzyl-5-bromo-2-pyridyl trifluoromethanesulfonate, 1.8 g of (3R,4R)-3,4-dihydroxypyrrolidine acetate, 3 ml of 1,8-diazabicyclo[5.4.0]-7-undecene and 5 ml of tetrahydrofuran was heated under stirring for 3 hours in an oil bath kept at 70° C. in a nitrogen atmosphere. After cooling as it was, the reaction mixture was extracted with ethyl acetate-water. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was subjected to silica gel column chromatography and eluted with 10% methanol/ethyl acetate, to give 1.67 g of the target compound.

Workup

  1. temperaturewas heated
  2. customkept at 70° C. in a nitrogen atmosphere
  3. temperatureAfter cooling as it
  4. extractionthe reaction mixture was extracted with ethyl acetate-water
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. washeluted with 10% methanol/ethyl acetate

Sources & evidence

ORD record
ord-1377c9282e6e4e8eb1671bc46fd259eb
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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