1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- → (S)-(-)-N-Boc-prolinol

HRID 1780292Notes

Reaction equation

HRID 1780292 reaction equation
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10](O)=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>C1COCC1>[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

3

Reactant 1

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

Product 1

HCID 643448(S)-(-)-N-Boc-prolinol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-BOC-(S)-proline (Sigma Chemical Co., 12.97 g, 60.02 mmol) was dissolved in anhydrous THF and brought to 0° C. with stirring. Borane/THF complex was added dropwise via syringe over a 10 minute period. The reaction mixture was stirred at room temperature for 1 hour, then the reaction was quenched slowly with saturated NaHCO3 and stirred for an additional hour. The solvent was removed in vacuo, and the residue was diluted with H2O. The desired compound was extracted from the aqueous phase with Et2O (3×). The organic layer was then washed with brine (2×) dried (MgSO4) and evaporated.

Workup

  1. custombrought to 0° C.
  2. additionBorane/THF complex was added dropwise via syringe over a 10 minute period
  3. stirringThe reaction mixture was stirred at room temperature for 1 hour
  4. customthe reaction was quenched slowly with saturated NaHCO3
  5. stirringstirred for an additional hour
  6. customThe solvent was removed in vacuo
  7. additionthe residue was diluted with H2O
  8. extractionThe desired compound was extracted from the aqueous phase with Et2O (3×)
  9. washThe organic layer was then washed with brine (2×)
  10. dry with materialdried (MgSO4)
  11. customevaporated

Sources & evidence

ORD record
ord-354a35f3d2394773a6349a43162ad6c9
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

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