Methanol → (S)-1-Allyloxymethyl-2-methylpropylamine

1.25 g (60%, 31.36 mmol) of sodium hydride were added to a solution of 3.00 g (15.68 mmol) of (S)-3-methyl-2-{[1-phenylmethylidene]amino}butan-1-ol in 28 ml of dry THF, and the mixture was stirred at RT for 45 min. Then 1.43 ml (16.46 mmol) of allyl bromide were added, and the mixture was stirred further at RT overnight. 20 ml of methanol were added to quench, and the mixture was acidified (pH 1) with 1N hydrochoric acid and stirred further. After 3 h, the reaction mixture was washed twice with dichloromethane, and the combined dichloromethane phases were extracted with 1N hydrochloric acid. The combined aqueous phases were basified with 1N sodium hydroxide solution (pH 14), saturated with sodium chloride and extracted three times with ethyl acetate, readjusting the pH after each extraction step. The combined organic phases were dried over sodium sulfate, filtered and concentrated, and taken up once in dichloromethane and again concentrated. 1.56 g of the title compound were obtained as a pale yellow liquid.

1. stirringthe mixture was stirred further at RT overnight
2. customto quench
3. stirringstirred further
4. waitAfter 3 h
5. washthe reaction mixture was washed twice with dichloromethane
6. extractionthe combined dichloromethane phases were extracted with 1N hydrochloric acid
7. extractionextracted three times with ethyl acetate
8. extractionafter each extraction step
9. dry with materialThe combined organic phases were dried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. concentrationagain concentrated

ORD record

ord-536021f9de4a4fa7aa4c0cc72aace6a2

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580777B2