(Iodomethyl)cyclopentane → Methyl 3-cyclopentyl-2-(4-methylsulfonylphenyl)propionate

HRID 1159464

Reaktionsgleichung

Reaktionsgleichung von HRID 1159464
[Li]CCCC.[CH3:6][O:7][C:8](=[O:20])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1.[CH:21]1([CH2:26]I)[CH2:25][CH2:24][CH2:23][CH2:22]1>C1COCC1.COC1SC(=O)N(CSP(OC)(OC)=S)N=1>[CH3:6][O:7][C:8](=[O:20])[CH:9]([C:10]1[CH:11]=[CH:12][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:14][CH:15]=1)[CH2:26][CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1

Komponenten

6

Edukt 3

HCID 2762531(Iodomethyl)cyclopentaneHCID 16640928Methyl 2-(4-(methylsulfonyl)phenyl)acetateHCID 178418339Butyllithium

Produkt 1

HCID 19261331Methyl 3-cyclopentyl-2-(4-methylsulfonylphenyl)propionate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 13709MethidathionLösungsmittel2×

Versuchsvorschrift

To a solution of diispropylamine (25 mmol, 3.6 mL) in 24 mL of THF and 7.5 mL of methidathion (DMTP) at −78° C. is added n-BuLi (25 mmol, 10 mL, 2.5 M in hexanes) and the mixture stirred for 15 min. 4-Methylsulfonylphenylacetic acid methyl ester (24 mmol, 5.47 g) in 24 mL of THF and 7.5 mL of DMTP is then added dropwise over 30 min and the reaction is stirred for 90 min further. Cyclopentylmethyliodide (28.9 mmol, 6.08 g) in 10 mL of THF is then added dropwise and the reaction is stirred for 1 h at −78° C. before allowing to warm to RT. After 12 h, the reaction is quenched with water, evaporated and then partitioned between ethyl acetate (EtOAc) and brine, and the organic solution is dried and evaporated to afford an oil. The crude material is chromatographed on silica (eluent: 5%→25% EtOAc in hexanes) to afford 3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-propionic acid methyl ester.

Aufarbeitung

  1. stirringthe reaction is stirred for 90 min further
  2. stirringthe reaction is stirred for 1 h at −78° C.
  3. waitAfter 12 h
  4. customthe reaction is quenched with water
  5. customevaporated
  6. custompartitioned between ethyl acetate (EtOAc) and brine
  7. customthe organic solution is dried
  8. customevaporated
  9. customto afford an oil
  10. customThe crude material is chromatographed on silica (eluent: 5%→25% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d8ef0e9e40c04f8c93c5fde6d48cf5da
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812167B2

Verknüpfte Notizen

Wird geladen…