Sodium Carbonate → (S)-ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate

To a solution of ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate (1 g, 2 mmol) and (R)-(+)-2-methyl-CBS-oxazaborolidine (0.11 g, 0.4 mmol) in toluene (7 mL) cooled to −20° C. was added a solution of freshly distilled catecholborane (0.29 mL, 2.6 mmol) in toluene (3 mL). After 3 h, saturated Na2CO3 (10 mL) was added, the mixture allowed to warm to room temperature and the layers separated. Following extraction with EtOAc, the combined organic layers were washed with additional saturated Na2CO3 (15 mL portions) until the washing was no longer colored and then once with saturated NH4Cl (15 mL). After drying over anhydrous MgSO4, the solution was absorbed onto silica gel in vacuo and purified by Yamazen column chromatography (10-65% EtOAc/Hex) to afford 0.61 g (61%, 98% ee) of the title compound as a colorless amorphous solid. 1H-NMR: 400 MHz, (CDCl3) δ: 7.72 (s, 1H); 7.69 (d, J=2.4 Hz, 1H); 7.50 (m, 2H); 7.37 (d, J=9.2 Hz, 1H); 7.30 (m, 2H); 7.19 (dd, J=9.2, 2.4 Hz, 1H); 5.21 (d, J=2 Hz, 1H); 4.21 (m, 2H); 3.25 (d, J=2 Hz, 1H); 2.53 (s, 3H); 1.22 (t, J=7.2 Hz, 3H).

1. customthe layers separated
2. extractionextraction with EtOAc
3. washthe combined organic layers were washed with additional saturated Na2CO3 (15 mL portions) until the washing
4. dry with materialAfter drying over anhydrous MgSO4
5. customthe solution was absorbed onto silica gel in vacuo
6. custompurified by Yamazen column chromatography (10-65% EtOAc/Hex)

ORD record

ord-c8a13706579a46b2bfc9d7fc36059ebd

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102614B2