Iodine → 2-Amino-2-methyl-3-phenylpropan-1-ol

Temperature

0 °C

To a solution of rac-α-methyl-phenylalanine (1.74 g, 9.71 mmol) in 30 mL THF at rt was added NaBH4 (0.92 g 24.27 mmol) in one portion. The solution was cooled to 0° C. Iodine (2.46 g, 9.71 mmol) in 5 mL THF was added dropwise over 30 min. After the addition was complete, the reaction was heated to reflux for 2 days. The reaction was then cooled to 0° C. and quenched by the addition of methanol until the bubbling subsided. The reaction mixture was acidified by the addition of 6N HCl until pH 1, stirred at 50° C. for 30 min and concentrated in vacuo. Purification using ion exchange chromatography (SCX cartridge) afforded 2-amino-2-methyl-3-phenylpropan-1-ol I as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.35-7.18 (m, 5H), 3.36 (A of AB, d, J=10.4 Hz, 1H), 3.31 (B of AB, d, J=10.4 Hz, 1H), 2.70 (s, 2H), 1.04 (s, 3H).

1. additionAfter the addition
2. temperaturethe reaction was heated
3. temperatureto reflux for 2 days
4. temperatureThe reaction was then cooled to 0° C.
5. customquenched by the addition of methanol until the bubbling
6. additionThe reaction mixture was acidified by the addition of 6N HCl until pH 1
7. concentrationconcentrated in vacuo
8. customPurification

ORD record

ord-6e751c5a07d04c5c90120bb79ce0f522

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354942B2