Potassium sodium tartarate → (2-(Methylthio)benzo[d]thiazol-6-yl)methanol

Temperature

-78 °C

To a stirred mixture of ethyl 2-(methylthio)benzo[d]thiazole-6-carboxylate (1.7 g, 6.6 mmol) from Step 2 of this Example in CH2Cl2 (50 mL) at −78° C. under argon was added 1 M diisobutyl aluminum hydride in CH2Cl2 (13.8 mL, 13.8 mmol) dropwise. After the mixture was stirred at −78° C. under argon for 3 h, it was allowed to warm slowly to 0° C. To the stirring mixture was added a saturated aq potassium sodium tartrate (50 mL) and the mixture was allowed to slowly warm to rt. After the mixture was stirred for 12 h, the organic layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with a gradient of 100% hexanes to 100% EtOAc to afford (2-(methylthio)benzo[d]thiazol-6-yl)methanol (1.05 g, 76%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.93 (m, 1H), 7.79 (d, J=8.3 Hz, 1H), 7.40 (dd, J=1.3, 8.3 Hz, 1H), 5.32 (t, J=5.7 Hz, 1H), 4.60 (d, J=5.8 Hz, 2H), 2.78 (s, 3H). LCMS (ESI) m/z 212 (M+H)+.

1. customat −78° C.
2. temperatureto warm slowly to 0° C
3. temperatureto slowly warm to rt
4. stirringAfter the mixture was stirred for 12 h
5. customthe organic layer was separated
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel flash chromatography
10. washeluting with a gradient of 100% hexanes to 100% EtOAc

ORD record

ord-60cb6177b41c45569bd2748e96676713

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952058B2