methyl (-)-(1S,2R,3S)-3-hydroxy-2-pentyl-1-cyclopentane acetate → rel-Methyl (1R,2S)-3-oxo-2-pentylcyclopentaneacetate

HRID 2374Notes

Reaction equation

HRID 2374 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][C@@H:4]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[C@H:3]1[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>CO>[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[C@H:3]1[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 1

HCID 11872415methyl (-)-(1S,2R,3S)-3-hydroxy-2-pentyl-1-cyclopentane acetate

Product 1

HCID 1738127rel-Methyl (1R,2S)-3-oxo-2-pentylcyclopentaneacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The intermediate methyl (-)-(1S,2R,3S)-3-hydroxy-2-pentyl-1-cyclopentane acetate presented a [α]20D =-16° (c=1.805, methanol)

Sources & evidence

ORD record
ord-4de432ae17d04f5487e4f075f169e736
Source dataset
uspto-grants-1998_03
Patent number
US05728866

Reaction notes

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