5-(Oct-1-ynyl)-2-tritylisoindoline → tert-Butyl 2,2-dimethyl-5-((6-octyl-3,4-dihydroquinolin-1(2H)-yl)methyl)-1,3-dioxan-5-ylcarbamate

HRID 710308Notes

Reaction equation

HRID 710308 reaction equation
[CH3:1][C:2]1([CH3:35])[O:7][CH2:6][C:5]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][C:15]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH2:10]2)[CH2:4][O:3]1.C(C1C=C2C(=CC=1)CN(C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C2)#CCCCCCC>>[CH3:35][C:2]1([CH3:1])[O:3][CH2:4][C:5]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][C:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH2:10]2)[CH2:6][O:7]1

Participants

3

Reactant 2

HCID 667262275-(Oct-1-ynyl)-2-tritylisoindolineHCID 86661763tert-Butyl 2,2-dimethyl-5-((6-(oct-1-ynyl)-3,4-dihydroquinolin-1(2H)-yl)methyl)-1,3-dioxan-5-ylcarbamate

Product 1

HCID 86661765tert-Butyl 2,2-dimethyl-5-((6-octyl-3,4-dihydroquinolin-1(2H)-yl)methyl)-1,3-dioxan-5-ylcarbamateYield 90%

Procedure

When the product of Step C is substituted for 5-(oct-1-ynyl)-2-tritylisoindoline in Example 2, Step E, the identical process afforded the title compound in 90% yield, as a colourless foam. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=6.9 Hz); 1.24 (m, 10H); 1.42 (m, 15H); 1.91 (m, 2H); 2.43 (tr, 2H, J=8 Hz); 2.75 (tr, 2H, J=6.5 Hz); 3.25 (tr, 1H, J=5.5 Hz); 3.64 (s, 2H); 3.8-3.99 (m, 4H); 4.7 (s, 1H); 6.7 (d, 1H, J=8.4 Hz); 6.76 (s, 1H); 6.82 (d, 1H, J=8.4 Hz).

Sources & evidence

ORD record
ord-6e86a10123814f8c91b3a379607e2fff
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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