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 → Tert-butyl-5-(4-(2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethoxy)-phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710353Notes

Reaction equation

HRID 710353 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][C:27]3[CH:28]4[CH2:33][CH:30]([CH2:31][CH:32]=3)[C:29]4([CH3:35])[CH3:34])=[CH:20][CH:19]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][C:27]3[CH:28]4[CH2:33][CH:30]([CH2:31][CH:32]=3)[C:29]4([CH3:35])[CH3:34])=[CH:22][CH:23]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 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-ylcarbamate

Product 1

HCID 131733951Tert-butyl-5-(4-(2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethoxy)-phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateYield 78.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the product of Step C (0.07 g, 0.14 mmol), and 10% Pd/C (0.05 g) in EtOH (5 ml) was stirred for 36 h under H2. The catalyst was removed by filtration through Celite pad and filtrate evaporated to dryness, to give the title product (0.055 g; 78%), as colourless paste. 1H-NMR (CDCl3) 1.02 (s, 3H); 1.18 (s, 3H); 1.39 (s, 3H); 1.41 (s, 3H); 1.46 (s, 9H); 1.84-2.35 (m, 13H); 2.45-2.6 (m, 2H); 3.65 (d, 2H, J=11.8 Hz); 3.84-3.92 (m, 4H); 4.94 (broad s, 1H); 6.77 (d, 2H, J=8.6 Hz); 7.05 (d, 2H, J=8.5 Hz).

Workup

  1. customThe catalyst was removed by filtration through Celite pad and filtrate
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-e0ec55f2a9c04ebb846cbda1434bae01
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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