Acetic acid 2-acetoxy-5-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-benzyl ester → 6-Cyclopentyl-6-[2-(4-hydroxy-3-methoxymethyl-phenyl)-ethyl]-dihydro-pyran-2,4-dione

HRID 858669Notes

Reaction equation

HRID 858669 reaction equation
[C:1](OC1C=CC(C#CC(C2CCCC2)(O)CC2OC(C)(C)OC(=O)C=2)=CC=1COC(=O)C)(=O)C.C1(C(O)(CC2OC(C)(C)OC(=O)C=2)C#CC2C=CC(C(C)(C)C#N)=C(F)C=2)CCCC1.[CH:66]1([C:71]2([CH2:79][CH2:80][C:81]3[CH:86]=[CH:85][C:84]([OH:87])=[C:83]([CH2:88][OH:89])[CH:82]=3)[O:76][C:75](=[O:77])[CH2:74][C:73](=[O:78])[CH2:72]2)[CH2:70][CH2:69][CH2:68][CH2:67]1>>[CH:66]1([C:71]2([CH2:79][CH2:80][C:81]3[CH:86]=[CH:85][C:84]([OH:87])=[C:83]([CH2:88][O:89][CH3:1])[CH:82]=3)[O:76][C:75](=[O:77])[CH2:74][C:73](=[O:78])[CH2:72]2)[CH2:70][CH2:69][CH2:68][CH2:67]1

Participants

4

Reactant 3

HCID 58762257Acetic acid 2-acetoxy-5-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-benzyl esterHCID 587626006-Cyclopentyl-6-[2-(4-hydroxy-3-hydroxymethyl-phenyl)-ethyl]-dihydro-pyran-2,4-dioneHCID 587626542-{4-[3-cyclopentyl-4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-3-hydroxybut-1-ynyl]-2-fluorophenyl)-2-methylpropanenitrile

Product 1

HCID 587627336-Cyclopentyl-6-[2-(4-hydroxy-3-methoxymethyl-phenyl)-ethyl]-dihydro-pyran-2,4-dione

Procedure

The title compound was prepared analogously to step 4 from Example A(97) where Acetic acid 2-acetoxy-5-[3-cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl) -3-hydroxy-but-1-ynyl]-benzyl ester (from step 2 below) was substituted in place of 2-{4-[3-cyclopentyl-4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-3-hydroxybut-1-ynyl]-2-fluorophenyl}-2-methylpropanenitrile. The product was obtained together with Example A(195) 6-Cyclopentyl-6-[2-(4-hydroxy-3-hydroxymethyl -phenyl)-ethyl]-dihydro-pyran-2,4-dione below. 1H NMR (400 MHz, CDCl3): δ 1.48–1.82 (m, 8H), 1.87–2.09 (m, 3H), 2.22–2.28 (m, 1H), 2.55–2.61 (m, 2H), 2.76 (s, 2H), 3.41 (s, 2H), 3.45 (2, 3H), 4.62 (2, 2H), 6.78–6.82 (m, 1H), 6.96–6.99 (m, 1H), 7.38 (s, 1H). ESIMS (MH−): 345.

Sources & evidence

ORD record
ord-686d83d0c56046859afb7ad43e332932
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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