4-Aminotricyclo[3.3.1.13,7]decane-1-methanol → 3-{2-[1-(3-Hydroxy-2,2-dimethyl-propionyl)-piperidin-4-yl]-ethoxy}-N-(5-hydroxymethyl-adamantan-2-yl)-benzamide
Reaction equation
[OH:1][CH2:2][C:3]([CH3:25])([CH3:24])[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][O:14][C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18](O)=[O:19])[CH2:8][CH2:7]1)=[O:5].[NH2:26][CH:27]1[CH:34]2[CH2:35][C:30]3([CH2:37][OH:38])[CH2:31][CH:32]([CH2:36][CH:28]1[CH2:29]3)[CH2:33]2>>[OH:1][CH2:2][C:3]([CH3:25])([CH3:24])[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][O:14][C:15]2[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=2)[C:18]([NH:26][CH:27]2[CH:28]3[CH2:36][CH:32]4[CH2:31][C:30]([CH2:37][OH:38])([CH2:35][CH:34]2[CH2:33]4)[CH2:29]3)=[O:19])[CH2:8][CH2:7]1)=[O:5]Participants
3
Procedure
Prepared from 3-{2-[1-(3-hydroxy-2,2-dimethyl-propionyl)-piperidin-4-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: 7.31-7.38 (m, 2H), 7.24-7.29 (m, 1H), 7.02 (d, 1H), 6.31-6.43 (m, 1H), 4.33-4.45 (m, 2H), 4.17-4.24 (m, 1H), 4.07 (t, 2H), 3.49 (s, 2H), 3.26 (d, 2H), 2.74-2.87 (m, 2H), 2.12-2.19 (m, 2H), 2.01-2.05 (m, 1H), 1.42-1.93 (m, 15H), 1.27 (s, 6H), 1.14-1.23 (m, 2H).
Sources & evidence
- ORD record
- ord-6426d9f98ee14ba28bd0c1a27c9fe0d5
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08334305B2
Reaction notes
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