Benzylamine → 3-methyl-3-nitro-N-benzylazetidine

Temperature

80 °C

A solution of 2-methyl-2-nitro-1,3-propanediol ditriflate [the product of step 1] (4.0 g, 10 mmol) in acetonitrile (70 ml) is cooled to 0° C.-5° C. and N-ethyl-diisopropylamine (3.23 g, 25 mmol) is added, followed by benzylamine (1.60 g, 15 mmol) and the mixture is stirred at a temperature of 80° C. for 12 hours. The cooled reaction mixture concentrated under reduced pressure, dissolved in ethyl acetate and transferred to a separating funnel. This is then washed with water (2×) and brine, dried (Na2SO4), filtered, and concentrated. The crude liquid product is used in the next step without further purification. The crude product is purified by chromatography using a 3:1 mixture of Hexane:Ethyl acetate as eluant; the product is obtained as an oil. 1H-NMR (CDCl3): 7.3 (m, 5H), 3.75 (d, 2H), 3.68 (s, 2H), 3.42 (d, 2H), 1.88 (s, 3H).

1. customThe cooled reaction mixture
2. concentrationconcentrated under reduced pressure
3. dissolutiondissolved in ethyl acetate
4. customtransferred to a separating funnel
5. washThis is then washed with water (2×) and brine
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude liquid product is used in the next step without further purification
10. customThe crude product is purified by chromatography
11. additiona 3:1 mixture of Hexane
12. customthe product is obtained as an oil

ORD record

ord-cf9fcf1f01494a498f493780eb3c4f7f

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278464B2