Diisobutylaluminum hydride → 2-Methoxy-6-methyl-3-nitro-4-pyridinemethanol

To a −70° C. solution of ester from step B (5.4 g, 22.5 mmol) in 140 mL of DCM was added 56.2 mL (56.2 mmol) of DIBAL-H (1M in hexane) by dropping funnel. The resulting solution was stirred for 1 h then warrned to room temperature over an additional hour. The reaction mixture was quenched by the careful addition of saturated NaK tartrate. Stirring was continued for 30 min then the solid was filtered and washed with 100 mL of DCM. The filtrate was extracted with 2×50 mL of saturated NaK tartrate then brine (25 mL). The yellow solution was concentrated and chromatographed (2:3 EtOAc/Hexane) to afford the desired alcohol as a yellow solid.

1. waitthen warrned to room temperature over an additional hour
2. customThe reaction mixture was quenched by the careful addition of saturated NaK tartrate
3. stirringStirring
4. waitwas continued for 30 min
5. filtrationthe solid was filtered
6. washwashed with 100 mL of DCM
7. extractionThe filtrate was extracted with 2×50 mL of saturated NaK tartrate
8. concentrationThe yellow solution was concentrated
9. customchromatographed (2:3 EtOAc/Hexane)

ORD record

ord-63844562a79f4e8e8b9aa0ccb2c5ccac

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610692B1