Triethylamine → Methyl {1-[1-(4-chlorophenyl)ethyl]azetidin-3-yl}(3,5-difluorophenyl)acetate

HRID 602676

Reaktionsgleichung

Reaktionsgleichung von HRID 602676
[NH:1]1[CH2:4][CH:3]([CH:5]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)[C:6]([O:8][CH3:9])=[O:7])[CH2:2]1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=O)[CH2:26]CCC)=[CH:21][CH:20]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([N:1]2[CH2:4][CH:3]([CH:5]([C:10]3[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=3)[C:6]([O:8][CH3:9])=[O:7])[CH2:2]2)[CH3:26])=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 906864'-ChlorovalerophenoneHCID 5049666Sodium triacetoxyborohydrideHCID 67065947Methyl azetidin-3-yl(3,5-difluorophenyl)acetate

Produkt 1

HCID 86609768Methyl {1-[1-(4-chlorophenyl)ethyl]azetidin-3-yl}(3,5-difluorophenyl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

A solution of 0.015 g (0.054 mmole) of methyl azetidin-3-yl(3,5-difluorophenyl)acetate, 0.020 g (0.101 mmol) of 1-(4-chlorophenyl)pentan-1-one and 0.015 mL (0.12 mmol) of triethylamine in 5 mL of dichloroethane was stirred at room temperature. After 5 min, 0.050 g (0.237 mmol) of sodium triacetoxyborohydride was added and the mixture was stirred at room temperature for 6 h. The reaction was quenched by addition of saturated K2CO3 solution and the mixture was partitioned between 10 mL ether and 2 mL saturated K2CO3 solution. The layers were separated and the organic layer was dried over Na2SO4, and concentrated. The residue was purified by reverse phase chromatography (Waters Xterra C18, 19 mm×10 mm) using a gradient of CH3CN—H2O-Et3N (20:80:0.1 to 60:40:0.1). Homogenous fractions were pooled and concentrated to afford the title compound as a mixture of isomers; Mass Spectrum: m/e=422 (M+1 35Cl and 424 (M+1 37Cl). Mass Spectrum: m/e=422 (M+1 35Cl and 424 (M+1 37Cl).

Aufarbeitung

  1. customThe reaction was quenched by addition of saturated K2CO3 solution
  2. customthe mixture was partitioned between 10 mL ether and 2 mL saturated K2CO3 solution
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by reverse phase chromatography (Waters Xterra C18, 19 mm×10 mm)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8a04fb2f3333474f9374b64141d63907
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906503B2

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