(1R,4S)-4-((tert-Butyldimethylsilyl)oxy)cyclopent-2-en-1-ol → (1s,3r)-1-Hydroxy-3-(ethyl-carboxymethoxy)-4-cyclopentene

HRID 2180024Notes

Reaction equation

HRID 2180024 reaction equation
[OH:1][C@H:2]1[CH:6]=[CH:5][C@@H:4]([O:7][Si](C(C)(C)C)(C)C)[CH2:3]1.CC[O:17][C:18]([CH3:20])=[O:19].[CH3:21][CH2:22]CCCC>>[OH:1][C@@H:2]1[CH:6]=[CH:5][C@H:4]([O:7][CH:20]([CH2:21][CH3:22])[C:18]([OH:17])=[O:19])[CH2:3]1

Participants

3

Reactant 2

HCID 10910904(1R,4S)-4-((tert-Butyldimethylsilyl)oxy)cyclopent-2-en-1-olHCID 21226206Ethyl acetate hexane

Product 1

HCID 69646949(1s,3r)-1-Hydroxy-3-(ethyl-carboxymethoxy)-4-cyclopenteneYield 77%

Procedure

Compound 14 was subjected to general procedure D. Yield=77%. TLC: Rf=0.29 (10% EtOAc/Hexane). 1H NMR (400 MHz, CDCl3): δ0.05 (s, 6H), 0.90 (s, 9H), 1.25 (t, 3H), 1.60 (m, 1H), 2.65 (m, 1H), 4.10 (s, 2H), 4.20 (q, 2H), 4.55 (m, 1H), 4.65 (m, 1H), 5.95 (m, 2H). Subsequent subjection of the product to general procedure I gave compound 15. Yield=79%. TLC: Rf=0.65 (EtOAc). 1H NMR (400 MHz, CDCl3): δ1.25 (t, 3H), 1.65 (m, 1H), 1.75 (s, 1H), 2.65 (m, 1H), 4.10 (s, 2H), 4.20 (q, 2H), 4.45 (m, 1H), 4.65 (m, 1H), 6.05 (m, 2H).

Sources & evidence

ORD record
ord-4877388d089e472e8164e58a727904cd
Source dataset
uspto-grants-2005_05
Patent number
US06887880B2

Reaction notes

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