(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

 Pakistan,  Sindh, 

Tharparkar District

Tharparkar District

Tharparkar District, is one of the twenty nine districts of Sindh province in Pakistan. It is headquartered at Mithi. It has the lowest Human Development Index of all the districts in Sindh. Wikipedia

Latitude and Longitude on Globe is 24.20.54.42N 70.43.05.87E

2nd Highest peak of Karoonjhar about 1067 ft Altitude.. Latitude and Longitude on Globe is 24.19.45.20N 70.43.19.69E

Highest peak of Karoonjhar 

Kakbanglow Rd near Mirpur Khas Sindh

Main gate of Mir Mehboob Ali Talpur (MPA) Mir Landhi Sindh

 

Main outer entrance of Mir Landhi village for residential area

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