反应详情

A solution of 3-methyl-3-nitro-N-benzylazetidine [the product of step 2] (3.9 g, 18.9 mmol) in ethyl acetate (370 ml) and 5% acetic acid (370 ml) is heated to reflux. Iron powder (5.25 g, 94.1 mmol) is added portion-wise every 5 minutes. After the addition is complete the reaction mixture is heated at reflux for 6 hours. The cooled reaction mixture is filtered through Hyflo, and the residue washed with ethyl acetate. The filtrate is transferred to a separating funnel and the organic layer separated and discarded. The aqueous layer is treated with 30% NaOH solution with ice cooling to give a pH of ca. 11. Dichloromethane is then added and the mixture vigorously stirred at ambient temperature for 10 minutes. This mixture is filtered through Hyfol, the filtrate transferred to a separating funnel and the organic layer is separated, dried (Na2SO4), filtered, and concentrated. The crude oily product (2.30 g, 69%) is used in the next step without further purification. 1H-NMR (CDCl3): 7.2 (m, 5H), 3.62 (s, 2H), 3.27 (d, 2H), 2.88 (d, 2H), 1.68 (bs, 2H), 1.4 (s, 3H).

1. additionAfter the addition
2. temperatureis heated
3. temperatureat reflux for 6 hours
4. customThe cooled reaction mixture
5. filtrationis filtered through Hyflo
6. washthe residue washed with ethyl acetate
7. customThe filtrate is transferred to a separating funnel
8. customthe organic layer separated
9. additionThe aqueous layer is treated with 30% NaOH solution with ice cooling
10. customto give a pH of ca. 11
11. filtrationThis mixture is filtered through Hyfol
12. customthe filtrate transferred to a separating funnel
13. customthe organic layer is separated
14. dry with materialdried (Na2SO4)
15. filtrationfiltered
16. concentrationconcentrated
17. customThe crude oily product (2.30 g, 69%) is used in the next step without further purification