Benzyl 3-hydroxypyrrolidine-1-carboxylate → (R)-(-)-1-CBZ-3-pyrrolidinol

HRID 723304Notes

Reaction equation

HRID 723304 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCCCCC.C(O)(C)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@@H:13]([OH:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 560953Benzyl 3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 11183628(R)-(-)-1-CBZ-3-pyrrolidinol

Reagents, catalysts & solvents 1

HCID 21585144Isopropanol hexaneSolvent

Procedure

The e.e. of N-benzyloxycarbonyl-3-hydroxypyrrolidine was measured by analytical HPLC with a chiral column [Chiralpak AS (Daicel), 250 mm×4.6 mm; eluent: hexane/isopropanol (100:4); flow rate: 1 ml/min; detection wavelength: 210 nm; retention times: 32.9 min for the (S)-form and 36.7 min for the (R)-form]. (R)-N-benzyloxycarbonyl-3-hydroxypyrrolidine was obtained in as 85% e.e.

Workup

  1. custom32.9 min

Sources & evidence

ORD record
ord-8b31dcc03b2d4b679416e8f182145ad6
Source dataset
uspto-grants-2006_11
Patent number
US07141412B2

Reaction notes

Loading…