تفاعل #324430

معادلة التفاعل

DMF

title compound

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

Cs2CO3

benzyl bromide

→

title compound

المردود 99.8%

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

المردود 99.8%

المذيبات

H2O

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe mixture extracted with EtOAc (2×)
2. 2
   غسيلThe combined organics were washed with brine (2×)
3. 3
   أخرىdried

الإجراء التجريبي

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).

المصدر