(1S,6R)-9-Oxa-3-azabicyclo[4.2.1]nonane

                       

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

1H NMR predict

(1S,6R)-9-Oxa-3-azabicyclo[4.2.1]nonane

EXPT  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.

13C NMR PREDICT

REFERENCES

http://onlinelibrary.wiley.com/doi/10.1002/ardp.19923250205/abstract;jsessionid=61D5B2D4DA952E04EF91805DA6314857.f03t02

http://pubs.acs.org/doi/full/10.1021/acs.oprd.6b00213

//////////////////Chiral Bicyclic Lactam

C1CC2CCNCC1O2

DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO .....FOR BLOG HOME CLICK HERE

Join me on Linkedin

Join me on Facebook FACEBOOK

Join me on twitter     

Join me on google plus Googleplus

 amcrasto@gmail.com