HCID 90388409, compound → HCID 90388581, compound

HRID 2201727Notes

Reaction equation

HRID 2201727 reaction equation
[CH3:1][O:2][CH2:3][O:4][C@@H:5]1[CH2:18][C@@H:17]2[C@H:8]([C@H:9]3[C@H:14]([CH2:15][CH2:16]2)[CH2:13][C@:12]2([CH3:24])[C:19]([C:22]#[N:23])=[CH:20][CH2:21][C@H:11]2[CH2:10]3)[CH2:7][CH2:6]1>CCOC(C)=O.[Pd]>[CH3:1][O:2][CH2:3][O:4][C@@H:5]1[CH2:18][C@@H:17]2[C@H:8]([C@H:9]3[C@H:14]([CH2:15][CH2:16]2)[CH2:13][C@:12]2([CH3:24])[C@@H:19]([C:22]#[N:23])[CH2:20][CH2:21][C@H:11]2[CH2:10]3)[CH2:7][CH2:6]1

Participants

4

Reactant 1

HCID 90388409HCID 90388409, compound

Product 1

HCID 90388581HCID 90388581, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 8 (180 mg, 0.6 mmol) in EtOAc (40 mL) was added Pd/C (100 mg) and hydrogenation was carried out under 7 atm H2 at room temperature for 3 h. The reaction was filtered through Celite® 545 which was washed with EtOAc (100 mL). Solvents were removed and the residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes) to afford compound 9 (172 mg, 94%): 1H NMR (CDCl3) δ 4.58 (s, 2H), 3.82-3.79 (m, 1H), 3.29 (s, 3H), 0.84 (s, 3H); 13C NMR (CDCl3) δ 121.4, 94.5, 71.8, 54.9, 48.4, 47.9, 46.7, 44.9, 44.4, 39.7, 38.1, 37.9, 36.6, 33.8, 33.7, 30.0, 28.3, 26.3, 26.2, 23.7, 14.2.

Workup

  1. filtrationThe reaction was filtered through Celite® 545 which
  2. washwas washed with EtOAc (100 mL)
  3. customSolvents were removed
  4. customthe residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bac28536526f48b58bcd1cf9b934d360
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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