1-Octyne → tert-Butyl-5-((4-(2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethoxy)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710352Notes

Reaction equation

HRID 710352 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:16]#[CH:17])[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C#CCCCCCC.I[C:28]1[CH:45]=[CH:44][C:31]([O:32][CH2:33][CH2:34][C:35]2[CH:36]3[CH2:41][CH:38]([CH2:39][CH:40]=2)[C:37]3([CH3:43])[CH3:42])=[CH:30][CH:29]=1.IC1C=C2C(=CC=1)CN(C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C2>>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:16]#[C:17][C:28]2[CH:29]=[CH:30][C:31]([O:32][CH2:33][CH2:34][C:35]3[CH:36]4[CH2:41][CH:38]([CH2:39][CH:40]=3)[C:37]4([CH3:43])[CH3:42])=[CH:44][CH:45]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 123701-OctyneHCID 115143851,1-Dimethylethyl N-(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamateHCID 667262485-Iodo-2-tritylisoindolineHCID 667267162-(2-(4-Iodophenoxy)ethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene

Product 1

HCID 131733950tert-Butyl-5-((4-(2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethoxy)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateYield 66%

Procedure

When tert-butyl-5-ethynyl-2,2-dimethyl-1,3-dioxan-5-ylcarbamate was substituted for 1-octyne and the product of Step B was substituted for 5-iodo-2-tritylisoindoline in Example 2, Step D, the similar process afforded the title compound in 66% yield, as pale paste. 1H-NMR (CDCl3) 0.80 (s, 3H); 1.25 (s, 3H); 1.41 (s, 3H); 1.46 (s, 9H); 2.06 (d, 2H, J=5.47 Hz); 2.21 (d, 2H, J=8.44 Hz); 2.33-2.44 (m, 4H); 3.93 (tr, 2H, J=7.0 Hz); 3.98 (d, 2H, J=11.4 Hz); 4.08 (d, 2H, J=11.5 Hz); 5.18 (s, 1H); 5.32 (s, 1H); 6.76 (d, 2H, J=8.8 Hz); 7.29 (d, 2H, J=8.7 Hz).

Sources & evidence

ORD record
ord-c58fd3c04b0f45c6b0bc334937fba5f4
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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