tert-Butyl-5-((3-1-admantanyl-4-isopropoxyphenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → tert-Butyl-5-(3-1-admantanyl-4-isopropoxyphenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710361Notes

Reaction equation

HRID 710361 reaction equation
[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]1([C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([C:28]34[CH2:37][CH:32]5[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]5)[CH2:29]3)[CH2:35]4)[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:38])[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([C:28]34[CH2:37][CH:32]5[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]5)[CH2:29]3)[CH2:35]4)[CH:19]=2)[CH2:13][O:12][C:11]([CH3:14])([CH3:15])[O:10][CH2:9]1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 131733955tert-Butyl-5-((3-1-admantanyl-4-isopropoxyphenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 131733956tert-Butyl-5-(3-1-admantanyl-4-isopropoxyphenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the product of Step B (0.035 g, 0.07 mmol), and 10% Pd/C (0.025 g) in EtOH (5 ml) was stirred for 16 h under H2. The catalyst was removed by filtration through Celite pad and the filtrate was evaporated to dryness to give the title product (0.035 g; 100%); as colourless paste. 1H-NMR (CDCl3) 1.35 (d, 6H, J=5.99 Hz); 1.4 (s, 3H); 1.42 (s, 3H); 1.46 (s, 9H); 1.91-1.97 (m, 2H); 2.03 (s, 3H); 2.09 (s, 6H); 2.45-2.5 (m, 2H); 3.67 (d, 2H, J=11.73 Hz); 3.89 (d, 2H, J=11.67 Hz); 4.54-4.62 (m, 1H); 4.93 (s, 1H); 6.72 (d, 1H, J=8.27 Hz); 6.92 (broad d, 1H, J=9.98 Hz); 6.99 (broad s, 1H).

Workup

  1. customThe catalyst was removed by filtration through Celite pad
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-88d72ca946c24674af5dad0833bb3ae4
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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