Reaction #324443

Reaction equation

title compound

(±)-1-[3-[5-Chloro-2-(1-phenyl-ethoxy)-phenoxy]-azetidin-1-yl]-2,2,2-trifluoro-ethanone

K2CO3

H2O

→

NH3 MeOH

title compound

Yield 68.0%

(±)-3-[5-Chloro-2-(1-phenyl-ethoxy)-phenoxy]-azetidine

Yield 68.0%

Solvents

MeOH

CH2Cl2

Conditions

Workup

1. 1
   Extractionthe mixture extracted with EtOAc (2×)
2. 2
   OtherThe combined organics were dried
3. 3
   Concentrationconcentrated

Procedure

To the title compound of Step B in MeOH (4 mL) was added K2CO3 (0.10 g, 0.72 mmol). After 15 h, H2O was added and the mixture extracted with EtOAc (2×). The combined organics were dried and concentrated. Silica gel chromatography (1-7 2M NH3/MeOH in CH2Cl2) gave 0.75 g (68% yield) of the title compound. MS (ESI): mass calcd. for C17H18ClNO2, 303.10; m/z found, 304.1 [M+H]+. 1H NMR (CDCl3): 7.38-7.31 (m, 4H), 7.28-7.24 (m, 1H), 6.72 (dd, J=8.6, 2.4 Hz, 1H), 6.67 (d, J=8.6 Hz, 1H), 6.55 (d, J=2.4 Hz, 1H), 5.23 (q, J=6.4 Hz, 1H), 4.99-4.93 (m, 1H), 3.95-3.81 (m, 4H), 1.66 (d, J=6.5 Hz, 3H).

Source