HCID 90388346, compound → HCID 78209994, compound

HRID 2201738Notes

Reaction equation

HRID 2201738 reaction equation
[CH3:1][C@@:2]12[C:18]([C:19]#[N:20])=[CH:17][CH2:16][C@@H:15]1[CH2:14][C@@H:13]1[C@H:4]([CH2:5][CH2:6][C@H:7]3[C@@:12]1([CH3:21])[CH2:11][CH2:10][C@H:9]([OH:22])[CH2:8]3)[CH2:3]2>CCOC(C)=O.[Pd]>[CH3:1][C@@:2]12[C@@H:18]([C:19]#[N:20])[CH2:17][CH2:16][C@H:15]1[CH2:14][C@@H:13]1[C@H:4]([CH2:5][CH2:6][C@H:7]3[C@@:12]1([CH3:21])[CH2:11][CH2:10][C@H:9]([OH:22])[CH2:8]3)[CH2:3]2

Participants

4

Reactant 1

HCID 90388346HCID 90388346, compound

Product 1

HCID 78209994HCID 78209994, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound 27 (60 mg, 0.2 mmol) in EtOAc (40 mL) was added Pd/C (30 mg). Hydrogenation was carried out under 5 atm H2 at room temperature for 3 h. The reaction was filtered through Celite 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 28 (54 mg, 90%): mp 145-147° C., [α]D25 +45.3 (c 0.23, CHCl3); 1H NMR (CDCl3) δ 4.05 (s, br, 1H), 2.27 (t, J=9.3 Hz, 1H), 0.89 (s, 3H), 0.78 (s, 3H); 13C NMR (CDCl3) δ 121.5, 66.5, 54.4, 48.6, 45.6, 44.3, 39.9, 39.2, 36.4, 35.7, 34.8, 32.1, 32.0, 28.8, 28.7, 26.6, 26.5, 24.1, 14.4, 11.2; IR νmax 3434, 2235, 1449 cm−1. Anal. Calcd for (C20H31NO): C, 79.68; H, 10.36; N, 4.65. Found: C, 79.47; H, 10.67; N, 4.77.

Workup

  1. filtrationThe reaction was filtered through Celite 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-5410c2f73d2949fca33cd7951da6993d
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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