Reaction #324439

Reaction equation

title compound

3-(4-chloro-2-formyl-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

m-CPBA

→

title compound

3-(4-chloro-2-hydroxy-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   Washthe reaction washed with saturated NaHCO3 (aq.) and 10% Na2S2O5 until KI paper negative
2. 2
   OtherThe combined organic layers were dried
3. 3
   workup.ADDITIONthen treated with MeOH (25 mL) and 1N NaOH (25 mL)
4. 4
   workup.WAITAfter 15 h
5. 5
   Extractionthen extracted with EtOAc (2×)
6. 6
   WashThe combined organic layers were washed with brine
7. 7
   Otherdried

Procedure

To a CH2Cl2 (25 mL) solution of the title compound of Step A (1.4 g, 4.3 mmol) was added 77% m-CPBA (1.4 g, 6.2 mmol). After 18 h, additional CH2Cl2 was added and the reaction washed with saturated NaHCO3 (aq.) and 10% Na2S2O5 until KI paper negative. The combined organic layers were dried then treated with MeOH (25 mL) and 1N NaOH (25 mL). After 15 h, the reaction was acidified with 1M KHSO4 then extracted with EtOAc (2×). The combined organic layers were washed with brine and dried to give the title compound as a white solid. 1H NMR (CDCl3): 6.96 (s, 1H), 6.82-6.80 (m, 1H), 6.73 (d, J=8.6 Hz, 1H), 5.62 (s, 1H), 4.91 (s, 1H), 3.66-3.46 (m, 4H), 2.20-2.11 (m, 2H), 1.47 (s, 9H).

Source