9-Oxa-3-azabicyclo[4.2.1]nonane

9-Oxa-3-azabicyclo[4.2.1]nonane; CAS 69928-94-5;
Molecular Formula:	C₇H₁₃NO
Molecular Weight:	127.18422 g/mol

(1R,3r,5S)-2′-((S)-1-Phenylethyl)-8-oxaspiro[bicyclo[3.2.1]octane-3,3′-[1,2]oxaziridine] (13)

(13) as a light orange oil. ¹H NMR (300 MHz, CDCl₃) δ 7.48–7.40 (m, 2H), 7.39–7.27 (m, 3H), 4.44–4.35 (m, 1H), 4.33–4.24 (m, 1H), 3.48 (q, J = 6.3 Hz, 1H), 2.33 (ddd, J = 12.9, 4.5, 3.5 Hz, 2H), 1.89 (d, J = 14.8 Hz, 1H), 1.71–1.60 (m, 1H), 1.55 (t, J = 4.2 Hz, 3H), 1.54–1.47 (m, 1H), 1.42–1.29 (m, 2H), 0.32 (ddd, J = 11.1, 6.9, 3.4 Hz, 1H) ppm. ¹³C NMR (75 MHz, CDCl₃) δ 141.0, 128.8, 128.1, 127.1, 82.0, 73.9, 73.3, 63.3, 43.0, 27.7, 27.6, 24.4 ppm.

(1S,6R)-3-((S)-1-Phenylethyl)-9-oxa-3-azabicyclo[4.2.1]nonan-4-one (14)

¹H NMR (300 MHz, CDCl₃) δ 7.29 (dddd, J = 15.5, 7.3, 5.0, 1.2 Hz, 5H), 6.18–6.04 (m, 1H), 4.38 (tt, J = 9.0, 7.7 Hz, 2H), 3.14 (d, J = 15.7 Hz, 1H), 2.92–2.75 (m, 3H), 2.11–1.82 (m, 4H), 1.50 (d, J= 7.1 Hz, 3H) ppm. ¹³C NMR (75 MHz, CDCl₃) δ 173.59, 140.25, 128.53, 127.37, 127.21, 75.61, 72.25, 51.03, 50.50, 50.44, 47.88, 28.75, 26.44, 16.01 ppm. [α]^21.8_D = 160.2° (c = 1, 100 mg/10 mL of MeOH).

(1S,6R)-3-((S)-1-Phenylethyl)-9-oxa-3-azabicyclo[4.2.1]nonane (15)

15 as a colorless oil. ¹H NMR (300 MHz, CDCl₃) δ 7.44–7.24 (m, 5H), 4.45 (t, J = 8.4 Hz, 1H), 4.38–4.28 (m, 1H), 3.85–3.74 (m, 1H), 2.77 (ddd, J = 19.5, 8.8, 4.1 Hz, 1H), 2.58 (dd, J = 10.6, 3.4 Hz, 2H), 2.43–2.28 (m, 1H), 2.23–2.06 (m, 1H), 2.02–1.84 (m, 4H), 1.44–1.29 (m, 4H) ppm. [α]^19.2_D = 25.683 (c = 0.989, 98.9 mg in 10 mL of MeOH).

(1S,6R)-9-Oxa-3-azabicyclo[4.2.1]nonane 11 as a white solid. ¹H NMR (300 MHz, CDCl₃) δ 9.88 (s, 1H), 9.34 (s, 1H), 4.71–4.31 (m, 2H), 3.56–2.88 (m, 4H), 2.49–1.70 (m, 6H) ppm.

ESI-MS found 128.0 (M + 1 ⁺. [α]^22.0_D = −10.88 (c = 0.92, 92 mg in 10 mL of MeOH).

OLD SYNTHESIS