Lithium aluminum hydride → (2S,4R)-4-Phenyl-2-pyrrolidinemethanol

HRID 557923Notes

Reaction equation

HRID 557923 reaction equation
[AlH4-].[Li+].[C:3]1([C@@H:9]2[CH2:13][NH:12][C@H:11]([C:14](OC)=[O:15])[CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCCC1>[C:3]1([C@@H:9]2[CH2:13][NH:12][C@H:11]([CH2:14][OH:15])[CH2:10]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 14102971HCID 14102971, compound

Product 1

HCID 57368261(2S,4R)-4-Phenyl-2-pyrrolidinemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium tetrahydroaluminate in tetrahydrofuran (1.00 M, 1.00 mL) was added to methyl (2S,4R)-4-phenylpyrrolidine-2-carboxylate (103.0 mg, 0.0005018 mol) in tetrahydrofuran (3.00 mL, 0.0370 mol) at 0° C. Then the ice-water bath was removed and the reaction mixture was stirred at rt for 1 h and was quenched with brine (1 mL). The resulting mixture was extracted with ethyl acetate (2×2 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give the desired product which was directly used in the next step without further purification.

Workup

  1. customThen the ice-water bath was removed
  2. customwas quenched with brine (1 mL)
  3. extractionThe resulting mixture was extracted with ethyl acetate (2×2 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1886924778be478cb073348f034705f8
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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