4-Aminotricyclo[3.3.1.13,7]decane-1-methanol → N-(5-Hydroxymethyl-adamantan-2-yl)-3-(2-pyridin-2-yl-ethoxy)-benzamide
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=O.[NH2:19][CH:20]1[CH:27]2[CH2:28][C:23]3([CH2:30][OH:31])[CH2:24][CH:25]([CH2:29][CH:21]1[CH2:22]3)[CH2:26]2>>[OH:31][CH2:30][C:23]12[CH2:22][CH:21]3[CH2:29][CH:25]([CH2:26][CH:27]([CH:20]3[NH:19][C:13](=[O:15])[C:12]3[CH:16]=[CH:17][CH:18]=[C:10]([O:9][CH2:8][CH2:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH:11]=3)[CH2:28]1)[CH2:24]2Participants
3
Procedure
Prepared from 3-(2-pyridin-2-yl-ethoxy)-benzoic acid and 4-amino-1-hydroxymethyladamantane to give the title compound as a mixture of two isomers. 1H NMR (400 MHz, CDCl3) δ: 8.88 (t, 1H), 8.28 (q, 1H), 7.84 (d, 1H), 7.75 (q, 1H), 7.32 (q, 2H), 7.23-7.29 (m, 1H), 6.93-7.04 (m, 1H), 6.44-6.51 (m, 1H), 4.44 (q, 2H), 4.14-4.22 (m, 1H), 3.61 (q, 2H), 3.27 (s, 1H), 2.10-2.24 (m, 2H), 1.98-2.09 (m, 2H), 1.55-1.94 (m, 8H), 1.45-1.54 (m, 1H), 1.40 (d, 1H).
Sources & evidence
- ORD record
- ord-e991f39a408147ae9d52a5900a14fd1d
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08334305B2
Reaction notes
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