HCID 54321067, compound → (S)-(-)-1-Benzyl-3-pyrrolidinol

HRID 2081946Notes

Reaction equation

HRID 2081946 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13]C(=O)CCCCC)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 54321067HCID 54321067, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After removal of hexane from the eluate containing (S)-N-benzyl-3-hydroxypyrrolidine under reduced pressure, vacuum distillation of the residue (bp. 160° C./3 mm Hg) yielded 2.21 g of (S)-N-benzyl-3-hexanoyloxypyrrolidine in colorless oily form. The specific rotation of this product was [a]D20 -15.3° (c=5, MeOH). This (S)-N-benzyl-3-hexanoyloxypyrrolidine was further hydrolyzed under alkaline conditions to produce the corresponding (S)-N-benzyl-3-hydroxypyrrolidine. After tosylation, the optical purity of this product was found by HPLC to be 100% e.e.

Sources & evidence

ORD record
ord-c1a29ba54f5f4edd966fc0ffe1ed4263
Source dataset
uspto-grants-1993_02
Patent number
US05187094

Reaction notes

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