Water → 3-(4-Cyclopropylmethoxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

HRID 40505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 40505
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12]S(C)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:17]1([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25](O)=[CH:24][CH:23]=2)[CH2:19][CH2:18]1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:25]2[CH:26]=[CH:27][C:22]([O:21][CH2:20][CH:17]3[CH2:18][CH2:19]3)=[CH:23][CH:24]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 10753243Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylateHCID 137554954-(Cyclopropylmethoxy)phenol

Produkt 1

HCID 866890083-(4-Cyclopropylmethoxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2.6 g (10.4 mmol) 3-methanesulfonyloxy-azetidine-1-carboxylic acid tert-butyl ester, 1.7 g (10.4 mmol) 4-cyclopropylmethoxy-phenol and 6.7 g (20.7 mmol) Cs2CO3 in 60 mL DMF is stirred for 12 h at 80° C. Water is added and the mixture is extracted with ethyl acetate (2×). The combined organic layers are washed with NaHCO3 solution and are dried over MgSO4. The solvent is evaporated and the residue is purified by column chromatography (silica gel; PE/ethyl acetate; gradient 9:1→8:2) to yield the desired product.

Aufarbeitung

  1. extractionthe mixture is extracted with ethyl acetate (2×)
  2. washThe combined organic layers are washed with NaHCO3 solution
  3. dry with materialare dried over MgSO4
  4. customThe solvent is evaporated
  5. customthe residue is purified by column chromatography (silica gel; PE/ethyl acetate; gradient 9:1→8:2)

Quellen und Nachweise

ORD-Eintrag
ord-01104f221ee24fd5bf1ed83c68ae1a3b
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530461B2

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