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

ORD record

ord-97a74ed396fc4e10b9bfc478755ad336

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06376499B1