Sulfuric Acid → HCID 118415298, compound

To a solution of (S)-2-(benzyl(methyl)amino)-2-cyclopentylacetaldehyde (7.9 g, 34 mmol, 1.0 eq) in MeOH (200 mL) was added concentrated H2SO4 (12.5 g, 127 mmol, 3.7 eq) drop-wise at 0° C. The reaction mixture was stirred for 10 min, then trimethylorthoformate was added (33 g, 311 mmol, 9.0 eq.) at 0° C. The reaction mixture was stirred at room temperature for 1 hour, and then heated to reflux for overnight. After cooled, the solvent was evaporated under reduced pressure, and the obtained residue was poured into sat NaHCO3 (300 mL, aq), extracted with ethyl acetate (300 mL). The organic layer was washed with brine, dried over sodium sulphate and evaporated to give a residue, which was purified by column chromatography on silica to yield the product 6 (8.6 g, 90% for two steps) as a light color oil.

1. stirringThe reaction mixture was stirred at room temperature for 1 hour
2. temperatureheated
3. temperatureto reflux for overnight
4. temperatureAfter cooled
5. customthe solvent was evaporated under reduced pressure
6. additionthe obtained residue was poured
7. extractionextracted with ethyl acetate (300 mL)
8. washThe organic layer was washed with brine
9. dry with materialdried over sodium sulphate
10. customevaporated
11. customto give a residue, which
12. customwas purified by column chromatography on silica

ORD record

ord-550acf226d5a440f97add5a926ab4a72

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260478B2