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

HRID 2180026Notes

Reaction equation

HRID 2180026 reaction equation
[O:1]([C@H:9]1[CH:13]=[CH:12][C@H:11]([OH:14])[CH2:10]1)[Si](C(C)(C)C)(C)C.CC[O:17][C:18]([CH3:20])=[O:19].[CH3:21][CH2:22]CCCC>>[OH:14][C@@H:11]1[CH:12]=[CH:13][C@@H:9]([O:1][CH:20]([CH2:21][CH3:22])[C:18]([OH:17])=[O:19])[CH2:10]1

Participants

3

Reactant 2

HCID 10878531(1R,4R)-4-((tert-Butyldimethylsilyl)oxy)cyclopent-2-en-1-olHCID 21226206Ethyl acetate hexane

Product 1

HCID 69646924(1s,3s)-1-Hydroxy-3-(ethyl-carboxymethoxy)-4-cyclopenteneYield 71%

Procedure

Compound 22 was subjected to general procedure D. Yield=71%. TLC: Rf=0.33 (10% EtOAc/Hexane). 1H NMR (400 MHz, CDCl3): δ0.05 (s, 6H), 0.90 (s, 9H), 1.30 (t, 3H), 1.90 (m, 1H), 2.20 (m, 1H), 4.05 (s, 2H), 4.20 (q, 2H), 4.75 (m, 1H), 5.05 (m, 1H), 6.00 (m, 2H). Subsequent subjection of the product to general procedure K gave compound 23. Yield=91%. TLC: Rf=0.25 (50% EtOAc/Hexane). 1H NMR (400 MHz, CDCl3): δ1.25 (t, 3H), 2.00 (m, 1H), 2.25 (m, 1H), 4.05 (s, 2H), 4.20 (q, 2H), 4.80 (m, 1H), 5.05 (m, 1H), 6.05 (m, 2H).

Sources & evidence

ORD record
ord-1b50eefd9d2849dd820f9bea90833795
Source dataset
uspto-grants-2005_05
Patent number
US06887880B2

Reaction notes

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