tert-Butyl 2,2-dimethyl-5-((5-octylisoindolin-2-yl)methyl)-1,3-dioxan-5-ylcarbamate → 2-Amino-2-((6-octyl-3,4-dihydroquinolin-1(2H)-yl)methyl)propane-1,3-diol
Reaction equation
CC1(C)[O:7][CH2:6][C:5]([NH:27]C(=O)OC(C)(C)C)([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][C:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH2:10]2)[CH2:4][O:3]1.CC1(C)OCC(NC(=O)OC(C)(C)C)(CN2CC3C(=CC=C(CCCCCCCC)C=3)C2)CO1>>[NH2:27][C:5]([CH2:8][N:9]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10]1)([CH2:6][OH:7])[CH2:4][OH:3]Participants
3
Reactant 2
Product 1
Procedure
When the product of Step D is substituted for tert-butyl 2,2-dimethyl-5-((5-octylisoindolin-2-yl)methyl)-1,3-dioxan-5-ylcarbamate in Example 2, Step G, the identical process afforded the title compound in 36% yield., as a colourless solid. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=7 Hz); 1.26 (m, 10H); 1.53 (m, 2H); 1.92 (m, 2H); 2.22 (broad s, 4H+H2O); 2.43 (tr, 2H, J=8 Hz); 2.76 (tr, 2H, J=6.4 Hz); 3.23 (s, 2H); 3.26 (tr, 2H, J=3.7 Hz); 3.51-3.61 (m, 4H); 6.7-6.87 (m, 3H).
Sources & evidence
- ORD record
- ord-1911991c74be48d7a771690f071d3b34
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181182B2
Reaction notes
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