(1S,4R)-4-hydroxy-2-cyclopentenyl acetate

¹H-NMR of (1S,4R)-4-hydroxy-2-cyclopentenyl acetate 

¹H NMR (300 MHz, CDCl₃): d_H: 1.65 (dt, ³J = 14.5, 4.0 Hz, 1 H, 5‑H_A), 2.05 (s, 3 H, CH₃), 2.09 (s, 1 H, OH), 2.80 (quint, J = 7.4 Hz, 1 H, 5‑H_B), 4.68-4.74 (m, 1 H, 4‑H), 5.46-5.52 (m, 1 H, 1‑H), 5.95-6.00 (m, 1 H, 2‑H), 6.08-6.13 (m, 1 H, 3‑H).

¹³C-NMR of (1S,4R)-4-hydroxy-2-cyclopentenyl acetate 

¹³C NMR (75 MHz, CDCl₃): d_C: 21.1 (COCH₃), 40.5 (5‑C), 74.7 (4‑C), 77.0 (1‑C), 132.5 (2‑C), 138.5 (3‑C), 170.8 (OCOCH₃).

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Al Shifa College of Pharmacy
Poonthavanam Post, Kizhattur Village
Perinthalmanna, Malappuram Dist
Kerala-679 325, India

(1S,3R)-3-Acetamidocyclohexane-1-carboxylic Acid

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  http://pubs.acs.org/doi/suppl/10.1021/acs.oprd.6b00146

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• Supporting Info

Gargnano, Italy

 

Gargnano

Town in Italy

Gargnano is a town and comune in the province of Brescia, in Lombardy. It is situated on the western shore of Lake Garda. The municipal territory includes the artificial Valvestino Lake, created in 1962. Wikipedia

 

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(1S,2S,5R,6S) -2-tert-Butoxycarbonylamino-bicyclo [3.1.0] hexane-2,6-dicarboxylic acid

Synthesis of (1S,2S,5R,6S) -2-tert-Butoxycarbonylamino-bicyclo [3.1.0] hexane-2,6-dicarboxylic acid

 A 1 L flask was charged with (1S,2S,5R,6S)-2-amino-bicyclo [3.1.0]hexane-2,6-dicarboxylic acid monohydrate (24.4 g, 0.12 mol, 1 equiv), dioxane (200 mL) and di-tert-butyl dicarbonate (52.4 g, 0.24 mol, 2.0 equiv). The suspension was vigorously stirred while sodium hydroxide 1N (420 mL, 3.5 equiv) was added. The mixture was stirred for 2 days, then 2.0 more equiv of di-tert-butyl dicarbonate were added and the reaction stirred for 3 additional days at rt. After 5 total days of reaction, water (400 mL) was added to dissolve the salts. The aqueous layer was extracted with ethyl acetate (4×100 mL) to remove the excess of reagent, and then taken to ca. pH=2 using 6 N hydrochloric acid. The acidic aqueous phase was then extracted using ethyl ether (6×200 mL). The combined organic layers were washed with water (250 mL) and brine (250 mL). After drying over sodium sulfate, solvents were evaporated in vacuum to afford a foamy white solid (26.4 g).

77% Yield. 

http://www.google.im/patents/US20040138304?cl=un

mp 100-101° C. 

[α]_D ²⁵=−41.1° (c=1.0, MeOH). 

¹H NMR (Methanol-d₄) δ: 4.98 (brs, 1H), 2.44 (dd, 1H, J=6.2, 2.6 Hz), 2.19-1.92 (m, 4H), 1.62 (t, 1H, J=2.8 Hz), 1.43 (s, 9H), 1.29 (m, 1H). 

¹³C NMR (Methanol-d₄) δ: 175.6, 175.2, 158.2, 60.1, 34.6, 31.9, 28.4, 27.2, 25.6, 20.6. MS (Neg. Electrospray): 284.2 (M⁺−H).

(1S, 2S,5R, 6S)-2-Allyloxycarbonylamino-bicyclo [3.1.0]hexane-2,6-dicarboxylic acid

Synthesis of (1S, 2S,5R, 6S)-2-Allyloxycarbonylamino-bicyclo [3.1.0]hexane-2,6-dicarboxylic acid

http://www.google.im/patents/US20040138304?cl=un

[0123] (1S,2S,5R,6S)-2-Amino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (15.0 g, 73.9 mmol) was slowly dissolved in 250 mL of saturated sodium bicarbonate. After complete solution, dioxane (100 mL) and allyl chloroformate (15.7 mL, 147.8 mmol) were added at room temperature and the mixture was stirred overnight. The reaction mixture was diluted with water (100 mL) and washed with three portions of ethyl acetate. The organic layer was extracted once with saturated sodium bicarbonate. The combined aqueous layers were acidified to pH 1 with 4N hydrochloric acid and extracted with two portions of ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated to provide the title compound as an oil (13.4 g, 67% yield).

¹H-NMR (CD₃OD)

δ: 6.01-5.82 (m, 1 H); 5.35-5.13 (m, 2 H); 4.51 (d, J=5.1 Hz, 2 H); 2.48-1.78 (m, 5 H); 1.69-1.62 (m, 1 H); 1.45-1.29 (m, 1 H).

 ¹³C-NMR (CD₃OD)δ: 176.7, 176.6, 158.3, 134.2, 117.4, 67.3, 66.3, 35.8, 33.1, 29.9, 27.0, 22.0.

(1S,3R)-3-Aminocyclopentanecarboxamide hydrochloride

(1S,3R)-3-Aminocyclopentanecarboxamide hydrochloride

Hydrogen chloride gas was bubbled through an ice-cooled solution of the amide from preparation 10 (438 mg, 1.92 mmol) in dichloromethane (50 ml) for 10 minutes, and the resulting suspension stirred at room temperature for 2 hours. The mixture was purged with nitrogen, then evaporated under reduced pressure. The residue was triturated with ether, to afford the title compound as a solid; 

¹H NMR (D₂O, 400 MHz) δ: 1.63-1.82 (m, 3H), 1.92-2.07 (m, 2H), 2.19 (m, 1H), 2.82 (m, 1H), 3.62 (m, 1H).