N-benzyl-3-pyrrolidinol → N-benzyl-3-pyrrolidinol

HRID 723301

Reaction equation

HRID 723301 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCCCCC.C(O)(C)C>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 69889N-benzyl-3-pyrrolidinol

Product 2

HCID 69889N-benzyl-3-pyrrolidinolHCID 1225011-(Phenylmethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 21585144Isopropanol hexaneSolvent

Procedure

The enantiomeric excess (e.e.) of N-benzyl-3-hydroxy-pyrrolidine was measured by analytical HPLC with a chiral column [Chiracel OB-H (Daicel), 250 mm×4.6 mm; eluent: hexane/isopropanol (98:2); flow rate: 0.5 ml/min; detection wavelength: 210 nm; retention times: min for the (R)-form and 43.5 min for the (S)-form]. N-benzyl-3-hydroxy-pyrrolidine obtained from the hydroxylation of N-benzylpyrrolidine catalysed by Pseudomonas oleovorans GPo1 has 52% e.e. (R).

Sources & evidence

ORD record
ord-60d7993c8a3f4a8f903ba9e674e59295
Source dataset
uspto-grants-2006_11
Patent number
US07141412B2

Linked notes

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