Cyclohexylphenylglycolic acid, (-)- → alpha-Cyclopentylmandelic acid, (+)-

Reaction equation

[CH:1]1([C@@:7]([OH:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3]C1.C([C@H]1OC(=O)[C@@](C2(O)CCCC2)(C2C=CC=CC=2)O1)(C)(C)C>>[CH:1]1([C@@:7]([OH:17])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8]([OH:10])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Reactant 2

HCID 777377Cyclohexylphenylglycolic acid, (-)-

HCID 11695185(2R,5S)-2-t-Butyl-5-(1-hydroxycyclopentyl)-5-phenyl-1,3-dioxolan-4-one

Product 1

HCID 948620alpha-Cyclopentylmandelic acid, (+)-

Procedure

This compound is prepared analogously to (R)-cyclohexyl-hydroxy-phenyl-acetic acid (Intermediate Siv) by replacing (2R,5S)-2-tert-butyl-5-(1-hydroxy-cyclohexyl)-5-phenyl-[1,3]dioxolan-4-one (step Siii) with (2R,5S)-2-tert-butyl-5-(1-hydroxy-cyclopentyl)-5-phenyl-[1,3]dioxolan-4-one.

Sources & evidence

ORD record: ord-18c3abac740d4c3bb29b82eefcfc0a44
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084463B2

Reaction notes

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