(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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TIMOLOL

(S)-1-[(1,1-dimethylethyl)amino]-3-{[4-morpholinyl)-1,2,5-thiadiazol-3yl]oxy}-2-propanol.

(S)-1-(tert-butylamino)-3-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol

Timolol maleate

The structural formula

UV - spectrum

Conditions : Concentration - 3 mg / 100 ml
Solvent designation schedule	Methanol	Water	0.1 M HCl	0.1M NaOH
The absorption maximum	299 nm	-	295 nm	296 nm
	210	-	197	206
ε	9070	-	8540	8920

IR - spectrum

Wavelength (μm)
Wavenumber (cm -1 )

Mass Spectrum

Spectrum (for the base)
The 10 largest peaks:
Peak	30	41	56	57	70	74	86	114	128	130
Meaning	376	85	107	168	72	144	999	102	83	214

SEE FULL CHAPTER AT

http://books.google.co.in/books?id=tQiZCwMb2jAC&pg=PA641&source=gbs_toc_r&cad=4#v=onepage&q&f=false

OR CLICK

Chapter 15 Timolol Maleate

Profiles of Drug Substances, Excipients and Related ...
books.google.com › Science › Chemistry › Organic



Front Cover. Klaus Florey. Academic Press, Sep 4, 1987 - Science - 770 pages ... Chapter 15 Timolol Maleate. 641. 

http://www.google.com/patents/US5231095

The crystal structure for S-timolol hemihydrate (single crystals from water-methylene chloride) was measured with a Enraf-Nonius CAD-4 diffractometer using graphite-monochromatized MoK.sub.α (0.71073 Å) and ω-2θ method at 21° C. The cell parameters and orientation matrix were determined from 18 reflections (6<θ<10°). The measuring rate (° min^-1) was 0.87-16.5, width (θ) 0.5+0.344tan θ and area (θ) 2-25. The following crystal data were obtained: spaced group monoclinic, C2 (No. 5); a=23.435(3) Å, b=6.384(8) Å, c=11.591(1) Å, α=90.00, β=103.081(1), γ=90.00, V=1687(3) Å, Z=2, d=1.281 gcm^-3.

The results obtained with a NMR spectrometer support the above obtained X-ray diffraction results (Instrument Bruker AC 250/Aspect 3000). ¹ H-NMR (solvent CDCl₃) δ (ppm): 1.09 (s, 9H), 2.0 (b, appr. 2.5H), 2.57 (d+d, 1H; 12.0 and 8.0 Hz), 2.80 (d+d, 1H; 12.0 and 4.0 Hz), 3.52 (m, 4H), 3.79 (m, 4H), 3.91 (m, 1H), 4.36 (d+d, 1H; 11.1 and 5.8 Hz), 4.47 (d+d, 1H; 11.1 and 4.1 Hz).

¹³ C NMR (solvent CDCl₃) 6 (ppm): 28.91 (g), 50.24 (s), 44.33 (t), 66.10 (d), 72.76 (t), 153.66 (s), 149.78 (s), 47.78 (t), 66.33 (t).

S-timol hemihydrate has also been analyzed thermogravimetrically (Perkin Elmer, TGS-2 thermogravimetric analyzer and attached differential scanning DSC 4 calorimeter). The TG graph indicates splitting off of the hydrate water at about 50° C., the DSC gives a melting point of 53.3° C.

Markku Per alampi, “S-timolol hemihydrate composition and method of preparation therefor.” U.S. Patent US5574035, issued October, 1986.

US5574035 

Patents

US 6174524, US 5231095

Links

• UV and IR Spectra. H.-W. Dibbern, RM Muller, E. Wirbitzki, 2002 ECV
• NIST / EPA / NIH Mass Spectral Library 2008
• Handbook of Organic Compounds. NIR, IR, Raman, and UV-Vis Spectra Featuring Polymers and Surfactants, Jr., Jerry Workman.Academic Press, 2000.
• Handbook of ultraviolet and visible absorption spectra of organic compounds, K. Hirayama. Plenum Press Data Division, 1967.

Timolol

Systematic (IUPAC) name
(S)-1-(tert-butylamino)-3-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol
Clinical data
Trade names	Timoptic
AHFS/Drugs.com	monograph
MedlinePlus	a602022
Pregnancy cat.	C (AU) C (US)
Legal status	℞ Prescription only
Routes	oral, Ophthalmic
Pharmacokinetic data
Bioavailability	60%
Metabolism	Hepatic: 80%
Half-life	2.5-5 hours
Excretion	Renal
Identifiers
CAS number	26839-75-8
ATC code	C07AA06 S01ED01
PubChem	CID 33624
IUPHAR ligand	565
DrugBank	DB00373
ChemSpider	31013
UNII	5JKY92S7BR
KEGG	D08600
ChEBI	CHEBI:9599
ChEMBL	CHEMBL499
Chemical data
Formula	C13H24N4O3S
Mol. mass	316.421 g/mol

SYNTHESIS

 doi:10.1021/jo00881a011.

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