(S)-2,3-dihydro-1,4-Benzodioxin-2-methanamine synthesis

9synthesis methods

Product Name:(S)-2,3-dihydro-1,4-Benzodioxin-2-methanamine
CAS Number:46049-49-4
Molecular formula:C9H11NO2
Molecular Weight:165.19

1H-Isoindole-1,3(2H)-dione, 2-[[(2S)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]-

71084-45-2
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(S)-2,3-dihydro-1,4-Benzodioxin-2-methanamine

46049-49-4
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Yield:46049-49-4 88%

Reaction Conditions:

with hydrazine hydrate in methanol; for 2 h;Reflux;

Steps:

2 (S)-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanamine (5)

To a solution of 4 (15 g, 50.8 mmol) in MeOH (300 mL) was added hydrazine hydrate (12.7 g, 254 mmol) and the mixture was stirred at reflux for 2 h.
After cooling, chloroform (500 mL) was added to the mixture and insolubles were removed by filtration.
The filtrate was concentrated in vacuo and treated with 0.5 N NaOH (200 mL), then extracted with ether.
The organic phase was washed with 0.5 N NaOH, water and brine, then dried over Na₂SO₄, filtered and concentrated in vacuo to obtain 5 as a colorless oil (7.36 g, 88%).
¹H NMR (400 MHz, CDCl₃) δ = 6.86 (m, 4H), 4.27 (dd, J = 2.4, 11.4 Hz, 1H), 4.13 (m, 1H), 4.02 (dd, J = 7.8, 11.2 Hz, 1H), 2.99 (dd, J = 3.2, 5.6 Hz, 2H); MS (ESI+) 166.1 (M+H)⁺.

References:

Takahashi, Bitoku;Funami, Hideaki;Iwaki, Takehiko;Maruoka, Hiroshi;Shibata, Makoto;Koyama, Makoto;Nagahira, Asako;Kamiide, Yoshiyuki;Kanki, Satomi;Igawa, Yoshiyuki;Muto, Tsuyoshi [Bioorganic and Medicinal Chemistry,2015,vol. 23,# 15,p. 4792 - 4803]