Sodium Hydroxide → (S)-(-)-1-Benzyl-3-pyrrolidinol

HRID 2081945Notes

Reaction equation

HRID 2081945 reaction equation
[OH-].[Na+].[CH2:3]([N:10]1[CH2:14][CH2:13][C@H:12]([O:15]C(=O)CCC)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>>[CH2:3]([N:10]1[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 15623660HCID 15623660, compound

Product 1

HCID 2733875(S)-(-)-1-Benzyl-3-pyrrolidinol

Procedure

Next, 50 ml of 1 N-NaOH was added to the (S)-N-benzyl-3-butyryloxypyrrolidine obtained above, and hydrolysis was performed while the mixture was heated. The reaction mixture was then extracted three times with 50 ml portions of methylene chloride, and the solvent was removed under reduced pressure to yield 3.31 g of (S)-N-benzyl-3-hydroxypyrrolidine. This crude product was vacuum-distilled at 111° C./2 mm Hg to yield 3.00 g of a colorless oily product. The NMR and IR spectra of this product coincided with those of the reference sample, and the results obtained by elemental analysis agreed well with the calculated values. The specific rotation of this product was [a]D20 -3.79 (c=5, MeOH), and the measurement by HPLC showed that the optical purity was 100% e.e. The specific rotation of the distilled (R)-N-benzyl-3-hydroxypyrrolidine was [a]D20 +3.73° (c=5, MeOH), and the optical purity was 99% e.e.

Workup

  1. customobtained above, and
  2. customhydrolysis
  3. temperaturewas heated
  4. extractionThe reaction mixture was then extracted three times with 50 ml portions of methylene chloride
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-29e9dccb07e244a3a95915f5ce98b97f
Source dataset
uspto-grants-1993_02
Patent number
US05187094

Reaction notes

Loading…