tert-Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamate → 2-Amino-2-((5-octylisoindolin-2-yl)methyl)propane-1,3-diol

HRID 710285Notes

Reaction equation

HRID 710285 reaction equation
CC1(C)[O:7][CH2:6][C:5]([NH:26]C(=O)OC(C)(C)C)([CH2:8][N:9]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:15]=3)[CH2:10]2)[CH2:4][O:3]1.CC1(C)OCC(NC(=O)OC(C)(C)C)(CNC2C=CC(CCCCCCCC)=CC=2)CO1>>[NH2:26][C:5]([CH2:8][N:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:15]=2)[CH2:10]1)([CH2:6][OH:7])[CH2:4][OH:3]

Participants

3

Reactant 2

HCID 66726563tert-Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamateHCID 66726792tert-Butyl 2,2-dimethyl-5-((5-octylisoindolin-2-yl)methyl)-1,3-dioxan-5-ylcarbamate

Product 1

HCID 461947412-Amino-2-((5-octylisoindolin-2-yl)methyl)propane-1,3-diolYield 70%

Procedure

When the product of Step F 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 70% yield. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=6.94 Hz); 1.25 (m, 10H); 1.56 (m, 2H); 2.56 (tr, 2H, J=7.86 Hz); 2.66 (broad m, 4H); 2.89 (s, 2H); 3.57 (s, 4H); 4.07 (s, 4H); 6.98 (s, 1H); 7.0 (d, 1H, J=7.6 Hz); 7.06 (d, 1H, J=7.6 Hz).

Sources & evidence

ORD record
ord-958ddf607389430dbda9d0d18c35ae52
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

Loading…