Sodium borohydride → HCID 60073977, compound

Temperature

-10 °C

Into a 10000 mL 4-necked, round bottomed flask was placed a solution of (S)-2-(4-methoxybenzylideneamino)propan-1-ol (693 g, 3.59 mol) in CH3OH (7000 mL). sodium borohydride (271.2 g, 7.17 mol) was added in several batches. The reaction mixture was cooled −10° C. After 2 hours at −10° C., the reaction was warmed to room temperature and concentrated under vacuum. The residual solution was diluted with 2000 mL of water and extracted three times with 3000 mL of ethyl acetate. The combined organic layer was dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by flash chromatography (silica, 1:4 ethyl acetate/petroleum ether) to afford the title compound as a yellow solid.

1. customInto a 10000 mL 4-necked, round bottomed flask was placed
2. temperaturethe reaction was warmed to room temperature
3. concentrationconcentrated under vacuum
4. additionThe residual solution was diluted with 2000 mL of water
5. extractionextracted three times with 3000 mL of ethyl acetate
6. dry with materialThe combined organic layer was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under vacuum
9. customThe residue was purified by flash chromatography (silica, 1:4 ethyl acetate/petroleum ether)

ORD record

ord-84621af76407480c87e63b5f12fffb69

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2