(1s,3r)-1-Hydroxy-3-(ethyl-carboxymethoxy)-4-cyclopentene → (1r,3r)-1-Hydroxy-3-(methyl-carboxymethoxy)-4-cyclopentene

HRID 2180027Notes

Reaction equation

HRID 2180027 reaction equation
[OH:1][C@@H:2]1[CH:6]=[CH:5][C@H:4]([O:7][CH:8]([CH2:12]C)[C:9]([OH:11])=[O:10])[CH2:3]1>CCOC(C)=O.CCCCCC>[OH:1][C@H:2]1[CH:6]=[CH:5][C@H:4]([O:7][CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH2:3]1

Participants

3

Reactant 1

HCID 69646949(1s,3r)-1-Hydroxy-3-(ethyl-carboxymethoxy)-4-cyclopentene

Product 1

HCID 69647030(1r,3r)-1-Hydroxy-3-(methyl-carboxymethoxy)-4-cyclopenteneYield 89%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Compound 15 was subjected to general procedure J. Yield=89%. TLC: Rf=0.31 (25% EtOAc/Hexane). 1H NMR (400 MHz, CDCl3): δ1.30 (t, 3H), 2.35 (m, 2H), 4.10 (s, 2H), 4.25 (q, 2H), 4.90 (m, 1H), 6.05 (m, 1H), 6.20 (m, 1H), 6.30 (m, 1H), 8.20 (d, 2H), 8.30 (d, 2H). Subsequent subjection of the product to general procedure E gave compound 30. Yield=91%. TLC: Rf=0.18 (50% EtOAc/Hexane). 1H NMR (400 MHz, CDCl3): δ2.00 (m, 1H), 2.25 (m, 1H), 3.75 (s, 3H), 4.05 (s, 2H), 4.80 (m, 1H), 5.05 (m, 1H), 6.05 (s, 2H).

Sources & evidence

ORD record
ord-29ba14c2d7f1448f869737814908a3eb
Source dataset
uspto-grants-2005_05
Patent number
US06887880B2

Reaction notes

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