Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamate → 2-Amino-2-((6-(benzyloxy)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)propane-1,3-diol

HRID 710384Notes

Reaction equation

HRID 710384 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][N:14]([CH2:19][C:20]1([NH:28]C(=O)OC(C)(C)C)[CH2:25][O:24]C(C)(C)[O:22][CH2:21]1)[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)OCC(NC(=O)OCCCC)(CNC2C=CC(CCCCCCCC)=CC=2)CO1>>[NH2:28][C:20]([CH2:19][N:14]1[CH2:13][CH2:12][C:11]2[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:10]=2)[CH2:15]1)([CH2:21][OH:22])[CH2:25][OH:24]

Participants

3

Reactant 2

HCID 68407657Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamateHCID 86661787tert-Butyl 5-((6-(benzyloxy)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 580788372-Amino-2-((6-(benzyloxy)-3,4-dihydroisoquinolin-2(1H)-yl)methyl)propane-1,3-diolYield 71%

Procedure

When the product of Step E was substituted for tea-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 71% yield, as a creamy solid. 1H-NMR (CDCl3) 2.5-2.9 (m, 10H+H2O); 3.4-3.6 (m, 4H); 3.72 (s, 2H); 5.01 (s, 2H); 6.6-6.8 (m, 2H); 6.81-6.95 (m, 1H); 7.25-7.45 (m, 5H).

Sources & evidence

ORD record
ord-290d8ffba9bd4d52969979d65b85ed25
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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