tert-Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamate → 2-Amino-2-((5-(3,4,5-trimethoxyphenethyl)indolin-1-yl)methyl) propane-1,3-diol
Reaction equation
CC1(C)[O:7][CH2:6][C:5]([NH:32]C(=O)OC(C)(C)C)([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][CH2:19][C:20]4[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=4)=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)[CH2:4][O:3]1.CC1(C)OCC(NC(=O)OC(C)(C)C)(CNC2C=CC(CCCCCCCC)=CC=2)CO1>>[NH2:32][C:5]([CH2:8][N:9]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][CH2:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=3)=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)([CH2:4][OH:3])[CH2:6][OH:7]Participants
3
Reactant 2
Product 1
Procedure
When the product of Step D was substituted for tert-butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamate in Example 1, Step B, the identical process afforded the title compound in 68% yield, as a creamy solid. 1H-NMR (CDCl3) 1.77 (broad s, 4H+H2O); 2.79 (s, 4H); 2.96 (tr, 2H, J=8.3 Hz); 3.07 (s, 2H); 3.44 (tr, 2H, J=8.3 Hz); 3.57-3.61 (m, 4H); 3.82 (m, 9H); 6.38 (s, 2H); 6.55 (d, 1H, J=7.95 Hz); 6.9 (d, 1H, J=7.95 Hz); 7.03 (s, 1H).
Sources & evidence
- ORD record
- ord-daa1ef51a70147848082d9f717b0e129
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181182B2
Reaction notes
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