tert-Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamate → 2-Amino-2-((6-((2'-(trifluoromethyl)biphenyl-4-yl)methoxy)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)propane-1,3-diol

HRID 710388Notes

Reaction equation

HRID 710388 reaction equation
CC1(C)[O:7][CH2:6][C:5]([NH:37]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]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:33]([F:36])([F:35])[F:34])=[CH:23][CH:22]=4)[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>>[NH2:37][C:5]([CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]([F:36])([F:34])[F:35])=[CH:23][CH:22]=3)[CH:15]=2)[CH2:10]1)([CH2:4][OH:3])[CH2:6][OH:7]

Participants

3

Reactant 2

HCID 66726563tert-Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamateHCID 86661789tert-Butyl 2,2-dimethyl-5-((6-((2'-(trifluoromethyl)biphenyl-4-yl)methoxy)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-1,3-dioxan-5-ylcarbamate

Product 1

HCID 461960222-Amino-2-((6-((2'-(trifluoromethyl)biphenyl-4-yl)methoxy)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)propane-1,3-diolYield 75%

Procedure

When the product of Step C 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 75% yield, as an off white solid. 1H-NMR (CDCl3+CD3OD) 2.5-3.9 (m, 16H+H2O); 5.02 (s, 2H); 6.69-6.91 (m, 3H); 7.25-7.53 (m, 7H); 7.68 (d, 1H, J=7.8 Hz).

Sources & evidence

ORD record
ord-bda90ea171e14a6995c69a73bc5978d9
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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