Ethanol → HCID 58473027, compound

HRID 1037476Notes

Reaction equation

HRID 1037476 reaction equation
[OH:1][C@H:2]1[C@H:6]([CH:7]=[CH2:8])[CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1.CCCCCCC.CCO>CO>[OH:1][C@@H:2]1[C@@H:6]([CH:7]=[CH2:8])[CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:3]1

Participants

5

Reactant 3

HCID 702EthanolHCID 8900HeptaneHCID 58473021HCID 58473021, compound2×

Product 1

HCID 58473027HCID 58473027, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The racemic mixture of trans-(±)-benzyl 3-hydroxy-4-vinylpyrrolidine-1-carboxylate (14 g) was resolved by using chiral HPLC (Chiralpak AD-H Heptane:EtOH:MeOH, 8:1:1). The desired enantiomerically enriched (3S,4R)-benzyl 3-hydroxy-4-vinylpyrrolidine-1-carboxylate (6.7 min; 6.3 g, >99.5% ee) and undesired (3R,4S)-benzyl 3-hydroxy-4-vinylpyrrolidine-1-carboxylate (9.3 min; 6.7 g, 99.5% ee) were obtained with 92% recovery.

Sources & evidence

ORD record
ord-cc9866b434ba48ab8ccc52b02ca052ef
Source dataset
uspto-grants-2013_10
Patent number
US08546434B2

Reaction notes

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