HCID 71499446, compound → HCID 71499427, compound

HRID 633669Notes

Reaction equation

HRID 633669 reaction equation
[CH3:1][O:2][C:3]1[C@:10]2([CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[C:11](=[O:12])[C@@H:6]([C@:7]([CH3:28])([CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[C@@H:8]([O:18][CH2:19][O:20][CH3:21])[CH2:9]2)[C:5](=[O:29])[CH:4]=1>[Pd].CO>[CH2:13]([C@@:10]12[C:11](=[O:12])[C@@H:6]([C@:7]([CH3:28])([CH2:22][CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[C@@H:8]([O:18][CH2:19][O:20][CH3:21])[CH2:9]1)[C:5](=[O:29])[CH:4]=[C:3]2[O:2][CH3:1])[CH2:14][CH:15]([CH3:17])[CH3:16]

Participants

4

Reactant 1

HCID 71499446HCID 71499446, compound

Product 1

HCID 71499427HCID 71499427, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 1 dram vial equipped with a stir bar is charged with 14.9 mg (0.037 mmol, 1 equiv.) of starting material 50 followed by 370 μL of methanol. The vial was flushed with argon, and 8.5 mg of palladium (5 wt % on activated carbon, 0.004 mmol, 0.10 equiv.) was added. The vial was then flushed with hydrogen, and a balloon contained hydrogen was affixed to the vial through a rubber septum cap. The mixture was stirred for 25 min at which time the mixture was filtered through Celite®. The filter cake was rinsed with copious amounts of methanol, and the collected filtrate was concentrated. The crude product was purified by silica gel chromatography (Rf=0.25 in 9:1 hexane:ethyl acetate), affording 14.5 mg (92% yield) of 55 as a clear oil. 1H NMR (500 MHz, CDCl3) δ ppm 5.69 (s, 1H), 4.58 (dd, J=6.9, 52.4 Hz, 2H), 3.80 (s, 3H), 3.59 (dd, J=5.4, 11.3 Hz, 1H), 3.33 (s, 3H), 3.15 (s, 1H), 2.20 (dd, J=5.4, 13.4 Hz, 1H), 1.79 (dt, J=4.5, 12.6 Hz, 1H), 1.72 (dd, J=11.3, 13.3 Hz, 1H), 1.66-1.48 (m, 3H), 1.31-1.14 (m, 4H), 1.14-1.05 (m, 1H), 0.90-0.85 (m, 15H). HRMS-ESI (m/z): [M+K]+ calculated for C24H40O5, 447.2507. found 447.2511.

Workup

  1. customA 1 dram vial equipped with a stir bar
  2. additionwas added
  3. customThe vial was then flushed with hydrogen
  4. customcap
  5. filtrationwas filtered through Celite®
  6. washThe filter cake was rinsed with copious amounts of methanol
  7. concentrationthe collected filtrate was concentrated
  8. customThe crude product was purified by silica gel chromatography (Rf=0.25 in 9:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-e76e6e8ffe47446bb4bf2bde93ffafc2
Source dataset
uspto-grants-2016_04
Patent number
US09321713B2

Reaction notes

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