Benzaldehyde → Methyl 1-(4-(3-(1-admantanyl)-4-methoxybenzyloxy)benzyl)azetidine-3-carboxylate

반응식

[C:1]12([C:11]3[CH:12]=[C:13]([CH:24]=[CH:25][C:26]=3[O:27][CH3:28])[CH2:14][O:15][C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:29][N:30]1CCC(=C2C3N=CC=CC=3CCC3C=CC=CC2=3)C[CH2:31]1.[CH:51](=O)C1C=CC=CC=1.Cl.N([CH2:62][C:63]([OH:65])=[O:64])C>>[C:1]12([C:11]3[CH:12]=[C:13]([CH:24]=[CH:25][C:26]=3[O:27][CH3:28])[CH2:14][O:15][C:16]3[CH:23]=[CH:22][C:19]([CH2:20][N:30]4[CH2:31][CH:62]([C:63]([O:65][CH3:51])=[O:64])[CH2:29]4)=[CH:18][CH:17]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

참가 물질

반응물 4

HCID 240Benzaldehyde

HCID 19861Azatadine

HCID 69483Glycine, N-methyl-, hydrochloride (1:1)

HCID 900025224-(3-(1-Admantanyl)-4-methoxybenzyloxy)benzaldehyde

생성물 1

HCID 66615154Methyl 1-(4-(3-(1-admantanyl)-4-methoxybenzyloxy)benzyl)azetidine-3-carboxylate수율 69%

실험 절차

When the product of Step B and azatadine 3 methylcarboxylate hydrochloride were substituted for 4-(5-(((4-fluorophenyl))-isopropyl)amino)methyl)thiophen-2-yl)benzaldehyde and sarcosine hydrochloride, respectively, in Example 22, Step C, the similar procedure afforded the title compound in 69% yield, as a pale paste. 1H-NMR (CDCl3) 7.24-7.20 (m, 2H); 7.16 (d, 2H, J=8.55 Hz); 6.91 (d, 2H, J=8.62 Hz); 6.85 (d, 1H, J=8.17 Hz); 4.92 (s, 2H); 3.82 (s, 3H); 3.69 (s, 3H); 3.52 (s, 2H); 3.49 (s, 1H); 3.47 (s, 2H); 3.31-3.24 (m, 3H); 2.08 (s, 6H); 2.04 (s, 3H); 1.75 (s, 6H).