HCID 60023916, compound → HCID 60023928, compound

HRID 1866822Notes

Reaction equation

HRID 1866822 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([CH:21]([CH3:23])[CH3:22])[C:9](=[O:20])/[CH:10]=[CH:11]\[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([CH:21]([CH3:22])[CH3:23])[C:9](=[O:20])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 60023916HCID 60023916, compound

Product 1

HCID 60023928HCID 60023928, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (740 mg of 10% wt/wt Pd/C) was added to a degassed solution of [(R)-(Z)-4-(3-cyano-phenyl)-1-isopropyl-2-oxo-but-3-enyl]-carbamic acid tert-butyl ester (7.4 g, 22.5 mmol, 1 equiv) in methanol (200 mL) at room temperature. The reaction mixture was thoroughly degassed and backfilled with hydrogen gas from a balloon. Hydrogenation proceeded at atmospheric pressure for 2.5 h. The (degassed) reaction mixture was then diluted with diethyl ether (300 mL), filtered through Celite, and washed with additional ether (2×100 mL). Upon concentration in vacuo, the residue was purified by (lash column chromatography (20% ethyl acetate-hexanes) to provide the ketone product as a white solid (5.9 g, 79%). ESMS [M+H]+: 331.2. 1H NMR (400 MHz, CDCl3) δ 7.51 (m, 2H), 7.46 (m, 1H), 7.41 (m, 1H), 5.07 (m, 1H), 4.24 (m, 1H), 2.98 (m, 2H), 2.86 (m, 2H), 2.11 (m, 1H), 1.45 (s, 9H), 0.98 (d, 3H, J=6.76 Hz), 0.74 (d, 3H, J=6.78 Hz). [α]D=+24.74 (c=0.95, CH3OH).

Workup

  1. customThe reaction mixture was thoroughly degassed and backfilled with hydrogen gas from a balloon
  2. customThe (degassed) reaction mixture
  3. additionwas then diluted with diethyl ether (300 mL)
  4. filtrationfiltered through Celite
  5. washwashed with additional ether (2×100 mL)
  6. concentrationUpon concentration in vacuo
  7. customthe residue was purified by (lash column chromatography (20% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-2735c687f39c453ea2e492193a6250a0
Source dataset
uspto-grants-2009_12
Patent number
US07629477B2

Reaction notes

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