tert-Butyl 3a,4,7,7a-Tetrahydro-1H-isoindole-2(3H)-carboxylate

tert-Butyl 3a,4,7,7a-Tetrahydro-1H-isoindole-2(3H)-carboxylate

    

tert-Butyl 3a,4,7,7a-Tetrahydro-1H-isoindole-2(3H)-carboxylate 

 as a brown oil. % Purity: 93.72% (GC);

 

¹H NMR (CDCl₃, 400 MHz) δ: 1.47 (s, 9H), 1.89–194 (m, 2H), 2.20–2.33 (m, 4H), 3.08 (dd, J₁ = 6.2 Hz, J₂= 10.2 Hz, 1H), 3.17 (dd, J₁ = 4.8 Hz, J₂ = 10.4 Hz, 1H), 3.37–3.43 (m, 2H), 5.65 (s, 2H);

 

¹³C NMR (CDCl₃, 100 MHz) δ: 24.63, 24.68, 28.49, 33.35, 34.23, 50.86, 50.92, 78.88, 124.19, 124.50, 155.22;

 

IR (CHCl₃): ν = 756, 1128, 1170, 1217, 1411, 1685, 2937, 2978, 3009 cm^–1;

 

TOFMS: [C₁₃H₂₁NO₂ + H⁺]: calculated 224.1645, found 168.0958 (M-tBu + H)⁺ (100%), 246.1382 (M + Na)⁺ (5%).

 

GC conditions were as follows for compound 4; Agilent GC-FID 7890A, column: ZB-5MSi (30 m X 0.32 mm, 0.25 µm) with injector temperature 250 ºC and detector temperature 280 ºC, diluent was Methanol, Oven temperature was at 70 ºC isocratic for 3 min. then raised up to 250 ºC @ 20 ºC/min then 15 min. hold.

 

 

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.6b00399

http://pubs.acs.org/doi/full/10.1021/acs.oprd.6b00399

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4,6,7,8,9,10-hexahydro-1H-6,10-methanopyrazino[2,3-h][3]benzazepine-2,3-dione.

Chemical structures of Varenicline Tartrate and degradant product (DP-I).........4,6,7,8,9,10-hexahydro-1H-6,10-methanopyrazino[2,3-h][3]benzazepine-2,3-dione.

(A) ¹H NMR spectrum of DP-I. (B) Proton decoupled ¹³C NMR spectrum of DP-I.


UHPLC-ToF MS⁺ of DP-I.

The impurity obtained as pale white crystals. mp 71–73. 

RP-UHPLC, tR = 1.8 min (98.5% purity).

MS (ESI, 70 eV): [M + H⁺] m/z 244. 

FT-IR (KBr), v, cm⁻¹ 3371, 3319, 3279, 3173, 3005, 2808, 1696, 1678, 1588, 1406, 1388, 1338, 1305, 1264, 1135, 1067, 873, 790, 680, 569, 485.

¹H NMR (400 MHz, DMSO-d₆ +D₂O, TMS): δ 7.2 (s, 2H, H-7,8), 3.1–3.4 (m, 6H, H-11,13,14 & 16),2.3 (m, 1H, H-12), 2.0 (d, 1H, 11.2 Hz, H-12).

¹³C NMR (100 MHz, DMSO-d₆, TMS): δ 173.8 (C-2,3), 155.1 (C-5,6), 137.6 (C-9,10), 125.1 (C-7,8), 38.8 (C-11), 37.9 (C-12), 38.8 (C-13), 45.8 (C-14), 48.6 (C-16).

UHPLC ToF MS+: m/z [M + H⁺].Calcd for C₁₃H₁₃N₃O₂: 244.1086; found: 244.1082.

Based on the above spectral data, the molecular formula of DP-I is C₁₃H₁₃N₃O₂ and the corresponding structure was characterized as 4,6,7,8,9,10-hexahydro-1H-6,10-methanopyrazino[2,3-h][3]benzazepine-2,3-dione.

PMC full text:

Sci Pharm. 2012 Apr-Jun; 80(2): 329–336. Published online 2012 Mar 20. doi:  10.3797/scipharm.1201-08

http://dx.doi.org/10.3797/scipharm.1201-08

1-((2 S ,3 S )-3-(( R )-2,2-dimethyl-1,3-dioxolan-4-yl )-2,3-dihydroxypropyl)-7,7,8,9- tetramethyl-6,7-dihydro-1H,5H-pyrid o[1,2,3-de]quinoxaline-2,3-dione

1-((2 S ,3 S )-3-(( R )-2,2-dimethyl-1,3-dioxolan-4-yl )-2,3-dihydroxypropyl)-7,7,8,9- tetramethyl-6,7-dihydro-1H,5H-pyrid o[1,2,3-de]quinoxaline-2,3-dione

TAKE A TOUR\


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1-Allyl-7,7,8,9-tetramethyl-6,7-dihydro-1H,5H- pyrido[1,2,3-de]quinoxaline-2,3-dione

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 1-Allyl-7,7,8,9-tetramethyl-6,7-dihydro-1H,5H- pyrido[1,2,3-de]quinoxaline-2,3-dione

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Urmia University is a public university in the city of Urmia, West Azerbaijan province, Iran. The university has six campuses, seven schools, more than 14,000 students, and exclusive research centers ... Wikipedia

Urmia is situated on a fertile plain called Urmia Plain, on western side of Lake Urmia and eastern side of Turkish border and marginal range of mountains.




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