tert-Butyl 2,2-dimethyl-5-((5-octylisoindolin-2-yl)methyl)-1,3-dioxan-5-ylcarbamate → 2-Amino-2-((6-octyl-3,4-dihydroisoquinolin-2(1H)-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[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:15]=3)[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[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:15]=2)[CH2:10]1)([CH2:6][OH:7])[CH2:4][OH:3]Participants
3
Reactant 2
Product 1
Procedure
When the product of Step F 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 68% yield., as a colourless solid. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=6.9 Hz); 1.26 (m, 10H); 1.54 (m, 2H); 2.48-3 (m, 3H); 3.54 (s, 4H); 3.76 (s, 2H); 6.7 p-7.06 (m, 3H).
Sources & evidence
- ORD record
- ord-6a89451e16c34009bcdfdf8d8e7e0ac0
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181182B2
Reaction notes
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