Sodium cyanoborohydride → HCID 59775197, compound

To a solution of 3-(4-fluoro-3-methylphenyl)propanal (1.0 g, 6 mmol) in 20 mL MeOH was added MeNH2HCl (556 mg, 7.2 mmol) followed by NaBH3CN (452 mg, 7.2 mmol) at room temperature. The mixture was stirred for 2 h at the room temperature. The reaction was quenched by pouring into 20 mL 5% aqueous NaOH and diluted with ethyl acetate. The mixture was extracted with more ethyl acetate (3×15 mL) and the combined organic layers washed with brine (2×10 mL) and dried over Na2SO4. The mixture was concentrated under reduced pressure and the product isolated by flash column chromatography eluting with 0% to 10% MeOH/DCM to provide 461 mg of the title compound as an colorless oil.

1. customThe reaction was quenched
2. additionby pouring into 20 mL 5% aqueous NaOH
3. additiondiluted with ethyl acetate
4. extractionThe mixture was extracted with more ethyl acetate (3×15 mL)
5. washthe combined organic layers washed with brine (2×10 mL)
6. dry with materialdried over Na2SO4
7. concentrationThe mixture was concentrated under reduced pressure
8. customthe product isolated by flash column chromatography
9. washeluting with 0% to 10% MeOH/DCM

ORD record

ord-18a5a0b9c2ea476f93b1feee8b968ee8

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879911B2