AcetaMide, N-[2-hydroxy-1-(hydroxyMethyl)-1-(1,2,3,4-tetrahydro-6-octyl-2-naphthalenyl)ethyl]- synthesis
- Product Name:AcetaMide, N-[2-hydroxy-1-(hydroxyMethyl)-1-(1,2,3,4-tetrahydro-6-octyl-2-naphthalenyl)ethyl]-
- CAS Number:945632-83-7
- Molecular formula:C23H37NO3
- Molecular Weight:375.54
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Yield:945632-83-7 33%
Reaction Conditions:
Stage #1: 2-acetylamino-2-(6-octyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-malonic acid diethyl esterwith lithium borohydride in tetrahydrofuran at 0 - 20; for 48 h;
Stage #2: with water in tetrahydrofuran;ethyl acetate;
Steps:
6
Example 6; N-r2-Hvdroxy- 1 -hydroxymethyl-l-Cβ-octyl- 1 ,2,3,4-tetrahydro-naphthalen-2- ylVethy?-acetamide (7); [00167] Lithium borohydride (2M solution in THF, 0.88 ml, 1.76 mmol) was added to compound 6 (200 mg, 0.44 mmol) in 5 ml THF at 00C. The reaction mixture was stirred at room temperature for 48 hours and diluted with 40 ml ethyl acetate. The solution was washed with brine (2x20 mL) and dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography (Silica gel, 4% MeOH in CH2Cl2) to provide 55 of mg compound 7 (33%).[00168] 1H NMR (300MHz, CDCl3) δ 0.88 (t, 3H, J = 6.56Hz), 1.29 (m, 10H), 1.57 (p, 2H, J = 6.25Hz), 1.94-1.98 (m, 2H), 2.05 (s, 3H), 2.33 (m, IH), 2.51 (t, 2H, J = 7.32), 2.60-2.85 (m, 4H), 3.69 (d, 2H, J = 11.61), 3.89 (dd, 2H, J = 11.61Hz, 7.25Hz), 6.22 (s, IH), 6.88-6.99 (m, 3H); 13C NMR δ 14.38, 22.92, 24.20, 24.35, 29.52, 29.66, 29.73, 29.95, 30.32, 31.94, 32.14, 35.78, 38.26, 63.55, 64.34, 64.46, 126.18, 128.85, 129.30, 133.06, 136.22, 140.75, 172.40.
References:
WO2007/92638,2007,A1 Location in patent:Page/Page column 33
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