Benzylamine → (3R,4R)-1-Benzylpyrrolidine-3,4-diol

HRID 1091300Notes

Reaction equation

HRID 1091300 reaction equation
S(O[CH2:12][C@H:13]([C@@H:15]([CH2:17]OS(C1C=CC(C)=CC=1)(=O)=O)[OH:16])[OH:14])(C1C=CC(C)=CC=1)(=O)=O.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])O.[Na+]>O1CCOCC1>[CH2:29]([N:36]1[CH2:12][C@@H:13]([OH:14])[C@H:15]([OH:16])[CH2:17]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 516892Sodium BicarbonateHCID 11037390HCID 11037390, compound

Product 1

HCID 7021491(3R,4R)-1-Benzylpyrrolidine-3,4-diolYield 46%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 1,4-dioxane (20 mL) solution of 1,4-di-O-tosyl-D-threitol (9.15 g, 21.25 mmol), benzylamine (9.29 mL, 85.0 mmol) was added, and the mixture was heated to reflux under a nitrogen stream for 4 days while stirring. The reaction liquor was returned to room temperature, and then a saturated aqueous solution of sodium hydrogen carbonate (50 mL) was added. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by column chromatography using silica gel [NH(basic)-silica gel 100 g, ethyl acetate to chloroform/methanol (10/1)], to obtain the title compound (1.88 g, 46%) as an oily matter.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under a nitrogen stream for 4 days
  3. customwas returned to room temperature
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-1ad691f8654743a393e6b3c507efc988
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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