Methanol → (2R,3R)-3-amino-4-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}butan-2-ol

Temperature

70 °C

115 mg (0.18 mmol) of (2S,3R)-2-amino-3-hydroxy-N-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-yl}butyramide was dissolved in 3 ml of THF, and 272 μl (0.54 mmol) of 2M borane dimethyl sufide solution in THF were added at 70° C. under nitrogen atmosphere, and the mixture was subsequently stirred at 70° C. for 2 hours. In order to decompose the excess borane, 1 ml of MeOH was added dropwise. The reaction mixture was evaporated, and 1 ml of water and 1 ml of conc HCl were added to the oily residue. The mixture was stirred at room temperature for 2 h, rendered alkaline using 2 molar NaOH and extracted with ethyl acetate. The organic phase was dried and purified by column chromatography on silica gel.

1. additionwas added dropwise
2. customThe reaction mixture was evaporated
3. addition1 ml of water and 1 ml of conc HCl were added to the oily residue
4. stirringThe mixture was stirred at room temperature for 2 h
5. extractionextracted with ethyl acetate
6. customThe organic phase was dried
7. custompurified by column chromatography on silica gel

ORD record

ord-a468a7d1563045ec92a72c29b9501c12

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08907098B2