Tert-butyl-2,2-dimethyl-5-((3-((3,4,5-trimethoxyphenyl)ethynyl)-phenyl)ethynyl)-1,3-dioxan-5-ylcarbamate → tert-Butyl-2,2-dimethyl-5-(3-(3,4,5-trimethoxyphenethyl)phenethyl)-1,3-dioxan-5-ylcarbamate
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][CH:21]=[C:20]([C:24]#[C:25][C:26]3[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=3)[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][CH:21]=[C:20]([CH2:24][CH2:25][C:26]3[CH:27]=[C:28]([O:36][CH3:37])[C:29]([O:34][CH3:35])=[C:30]([O:32][CH3:33])[CH:31]=3)[CH:19]=2)[CH2:9][O:10][C:11]([CH3:15])([CH3:14])[O:12][CH2:13]1)([CH3:3])([CH3:2])[CH3:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of the product of Step B (0.09 g, 0.17 mmol) and 10% Pd/C (0.04 g) in EtOH (10 ml) was stirred for 36 h at room temperature under H2. The catalyst was removed by filtration through Celite pad and the filtrate was evaporated to dryness to give the title product (0.063 g; 70%), as colourless paste. 1H-NMR (CDCl3) 1.41 (s, 3H); 1.42 (s, 3H); 1.46 (s, 9H); 1.92-1.98 (m, 2H); 2.49-2.55 (m, 2H); 2.81-2.86 (m, 4H); 7.18 (tr, 1H, J=7.59 Hz). 3.67 (d, 2H, J=11.72 Hz); 3.80 (s, 6H); 3.83 (s, 3H); 3.88 (d, 2H, J=11.65 Hz); 5.01 (broad s, 1H); 6.37 (s, 2H); 6.98-7.01 (m, 3H).
Workup
- customThe catalyst was removed by filtration through Celite pad
- customthe filtrate was evaporated to dryness
Sources & evidence
- ORD record
- ord-0bd236a7149c49df9f8246ebb0d8b2b5
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181182B2
Reaction notes
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