Réaction #324430

Équation de réaction

DMF

title compound

3-(5-Bromo-2-hydroxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

Cs2CO3

benzyl bromide

→

title compound

Rendement 99.8%

3-(2-benzyloxy-5-bromo-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

Rendement 99.8%

Solvants

H2O

Conditions de réaction

Traitement

1. 1
   Extractionthe mixture extracted with EtOAc (2×)
2. 2
   LavageThe combined organics were washed with brine (2×)
3. 3
   Autredried

Mode opératoire

To a DMF (10 mL) solution of the title compound of Step C (0.52 g, 1.5 mmol), Cs2CO3 (0.54 g, 1.7 mmol) and KI (0.20 g, 1.20 mmol) was added benzyl bromide (0.20 mL, 0.29 g, 1.7 mmol). After 48 h, H2O was added and the mixture extracted with EtOAc (2×). The combined organics were washed with brine (2×) and dried. Silica gel chromatography (5-20% EtOAc in hexanes) gave 0.65 g (99%) of the title compound as a clear oil. 1H NMR (CDCl3): 7.42-7.36 (m, 3H), 7.34-7.31 (m, 2H), 7.03 (dd, J=8.6, 2.3 Hz, 1H), 6.81 (d, J=8.6 Hz, 1H), 6.70 (d, J=2.3 Hz, 1H), 5.09 (s, 2H), 4.88-4.83 (m, 1H), 4.26 (ddd, J=9.7, 6.5, 0.9 Hz, 2H), 4.05 (dd, J=9.8, 4.0 Hz, 2H), 1.45 (s, 9H).

Source