Methylamine → HCID 178448322, compound

A stirred solution of (S)-2-((S)-1-(2-bromophenyl)but-3-enylamino)-2-phenyl-ethanol (compound 2; 124 mmol, 42.8 g) in methanol (500 mL) and methylamine (680 mmol, 71.1 mL, 33% solution in ethanol) was treated dropwise with a solution of periodic acid (340 mmol, 77 g) in methanol (50 mL) with ice/water cooling to maintain an internal temp less than 25° C. The mixture was stirred at room temperature for 3 hours then left to stand overnight. The mixture was quenched with 2M aqueous sodium hydroxide (300 mL) to give a thick precipitate that was stirred for 1 hr then the methanol was removed under vacuum. The mixture was filtered through dicalite and the gelatinous cake washed water (200 mL), then methylene chloride (250 mL) was added. Layers were separated and the aqueous layer extracted with methylene chloride (200 mL). Combined extracts dried over sodium sulfate and evaporated to give crude (S,E)-N-benzylidene-1-(2-bromo phenyl)but-3-en-1-amine (31.65 g) as a yellow oil.

1. temperatureto maintain an internal temp less than 25° C
2. waitthen left
3. waitto stand overnight
4. customThe mixture was quenched with 2M aqueous sodium hydroxide (300 mL)
5. customto give a thick precipitate that
6. stirringwas stirred for 1 hr
7. customthe methanol was removed under vacuum
8. filtrationThe mixture was filtered through dicalite
9. washthe gelatinous cake washed water (200 mL)
10. additionmethylene chloride (250 mL) was added
11. customLayers were separated
12. extractionthe aqueous layer extracted with methylene chloride (200 mL)
13. dry with materialCombined extracts dried over sodium sulfate
14. customevaporated

ORD record

ord-306d70a71d064f0a99d10f24544c16dd

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188123B2