Sodium Hydroxide → (S)-2-(Methylamino)-3-phenylpropan-1-ol

Temperature

-5 °C

To a solution of N-methyl-L-phenylalanine (Sigma, 10 g, 55.8 mmol) in dry THF (600 mL) was added 3.18 g (83.7 mmol) lithium aluminium hydride at −5° C. The reaction mixture was stirred over night and cooled to −5° C. Additional 2.12 g (55.8 mmol) lithium alanate were added. The reaction mixture was refluxed overnight and cooled then to −5° C. To this mixture was added 21.5 ml NaOH solution (2N) drop by drop. and stirred at room temperature for additional 30 min. The mixture was filtered and the filtercake was washed with diethyl ether (50 mL). The filtrate was dried over MgSO4 and solvent was removed under reduced pressure to obtain the product 1b as light yellow solid.

1. temperatureThe reaction mixture was refluxed overnight
2. temperaturecooled
3. customto −5° C
4. stirringand stirred at room temperature for additional 30 min
5. filtrationThe mixture was filtered
6. washthe filtercake was washed with diethyl ether (50 mL)
7. dry with materialThe filtrate was dried over MgSO4 and solvent
8. customwas removed under reduced pressure

ORD record

ord-f29e3c5d87b34d7d8b453c16dcfaa10f

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08784775B2