4-Aminotricyclo[3.3.1.13,7]decane-1-methanol → 4-{2-[3-(5-Hydroxymethyl-adamantan-2-ylcarbamoyl)-phenoxy]-ethyl}-piperidine-1-carboxylic acid isopropylamide
Reaction equation
[CH:1]([NH:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][O:15][C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19]([OH:21])=O)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[NH2:25][CH:26]1[CH:33]2[CH2:34][C:29]3([CH2:36][OH:37])[CH2:30][CH:31]([CH2:35][CH:27]1[CH2:28]3)[CH2:32]2>>[CH:1]([NH:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([CH2:13][CH2:14][O:15][C:16]2[CH:24]=[CH:23][CH:22]=[C:18]([C:19](=[O:21])[NH:25][CH:26]3[CH:27]4[CH2:35][CH:31]5[CH2:30][C:29]([CH2:36][OH:37])([CH2:34][CH:33]3[CH2:32]5)[CH2:28]4)[CH:17]=2)[CH2:11][CH2:12]1)=[O:6])([CH3:2])[CH3:3]Participants
3
Procedure
Prepared from 3-[2-(1-isopropylcarbamoyl-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: 7.30-7.37 (m, 2H), 7.23-7.29 (m, 1H), 7.02 (d, 1H), 6.32-6.43 (m, 1H), 4.16-4.24 (m, 1H), 4.06 (t, 2H), 3.94-4.02 (m, 1H), 3.91 (d, 2H), 3.26 (d, 2H), 2.77 (t, 2H), 2.11-2.19 (m, 2H), 1.99-2.05 (m, 1H), 1.41-1.94 (m, 15H), 1.18-1.29 (m, 2H), 1.15 (d, 6H).
Sources & evidence
- ORD record
- ord-30bfd6f6f3254b2787398d98f2e15896
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08334305B2
Reaction notes
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