Lithium borohydride → 3-(Hydroxymethyl)benzonitrile

To a stirred, room temperature solution of the ester from above (2.05 g, 4.6 mmol) in MeOH (50 mL) was added LiBH4 (1.0 g, 50 mmol) in three portions. Effervescence was observed, and the mixture was stirred for 3.5 hours. The mixture was concentrated and 1 N NaOH (50 mL) was added to the resultant residue. The aqueous mixture was extracted with CH2Cl2 (3×50 mL). The organic extracts were combined, dried (Na2SO4), and concentrated. Purification of the crude material by column chromatography on silica gel (40 g, eluted with 5% NH4OH/5% MeOH/CH2Cl2) provided 4-3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-3-hydroxymethyl-benzonitrile (1.63 g, 86%) as a pale yellow solid.

1. concentrationThe mixture was concentrated
2. addition1 N NaOH (50 mL) was added to the resultant residue
3. extractionThe aqueous mixture was extracted with CH2Cl2 (3×50 mL)
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated
6. customPurification of the crude material by column chromatography on silica gel (40 g, eluted with 5% NH4OH/5% MeOH/CH2Cl2)

ORD record

ord-d545e0bec5184b8381c85e18362865a5

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07550484B2