Methyl p-toluenesulfonate → (+/-)-Benzyl 2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethylcarbamate

HRID 13923

Reaktionsgleichung

Reaktionsgleichung von HRID 13923
[O:1]1[CH:5]([CH2:6][NH2:7])[CH2:4][C:3]2[CH:8]=[CH:9][C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=3[C:2]1=2.C(N(C(C)C)CC)(C)C.Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27].CC1C=CC(S(OC)(=O)=O)=CC=1>>[O:1]1[CH:5]([CH2:6][NH:7][C:26](=[O:27])[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:4][C:3]2[CH:8]=[CH:9][C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=3[C:2]1=2

Komponenten

5

Edukt 4

HCID 6645Methyl p-toluenesulfonateHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11241138(+/-)-1-(2,3,6,7,8,9-Hexahydronaphtho[1,2-b]furan-2-yl)methanamine

Produkt 1

HCID 86598544(+/-)-Benzyl 2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethylcarbamateAusbeute 79,1 %

Versuchsvorschrift

Treatment of (±)-1-(2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-yl)methanamine (0.846 g, 4.16 mmol) with diisopropylethylamine (0.592 g, 4.58 mmol) followed by benzyl chloroformate (0.745 g, 4.37 mmol) generally according to the procedure described for Intermediate 7 provided 1.11 g (79%) of (±)-benzyl 2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethylcarbamate as a white solid. Rf=0.39 (silica, ethyl acetate:hexanes 1:4); mp 88-90° C.; 1H NMR (DMSO-d6) δH 7.49 (t, 1H); 7.33 (m, 4H); 6.87 (d, 1H); 6.50 (d, 1H); 5.02 (s, 2H); 4.76 (m, 1H); 3.20 (m, 3H); 2.83 (dd, 1H); 2.62 (s, 2H); 2.49 (m, 2H); 1.67 (m, 4H). Chiral HPLC separation of (±)-benzyl 2,3,6,7,8,9-hexahydronaphtho[1,2-b]furan-2-ylmethylcarbamate (Chiralcel OJ, isopropanol:hexane 9:1) provided two fractions. Fraction 1 (Rt=11.576 min, Chiralcel OD, isopropanol:hexanes 1:9); Fraction 2 (Rt=14.729 min, Chiralcel OD, isopropanol:hexanes 1:9).

Quellen und Nachweise

ORD-Eintrag
ord-037b887922de407fbf568451c5ed7526
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728155B2

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