Benzaldehyde → Methyl-1-(4-(2-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)ethoxy)benzyl)azetidine-3-carboxylate
Reaction equation
[CH3:1][C:2]1([CH3:20])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:9][CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.CN1CCC(=C2[C:36]3[N:37]=[CH:38][CH:39]=[CH:40]C=3CCC3C=CC=CC2=3)CC1.[CH:43](=[O:50])C1C=CC=CC=1.Cl.N(CC(O)=[O:56])C>>[CH3:43][O:50][C:40]([CH:39]1[CH2:38][N:37]([CH2:16][C:15]2[CH:18]=[CH:19][C:12]([O:11][CH2:10][CH2:9][CH:6]3[CH2:5][CH2:4][CH:3]4[CH2:8][CH:7]3[C:2]4([CH3:20])[CH3:1])=[CH:13][CH:14]=2)[CH2:36]1)=[O:56]Participants
5
Procedure
When the product of Step A 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 76% yield, as light yellow paste. 1H-NMR (CDCl3) 7.17 (d, 2H, J=8.56 Hz); 6.81 (d, 2H, J=8.61 Hz); 3.91 (t, 2H, J=1.98 Hz); 3.71-3.65 (m, 7H); 3.44-3.41 (m, 3H); 2.03-1.17 (m, 10H); 1.17 (s, 3H); 1.01 (s, 3H).
Sources & evidence
- ORD record
- ord-8b37d7ee37f8499ea1ab8bcd2619ec0e
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193716B2
Reaction notes
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