HCID 90388059, compound → HCID 90388303, compound

HRID 2201747Notes

Reaction equation

HRID 2201747 reaction equation
[OH:1][C@H:2]1[C@:6]2([CH3:20])[CH2:7][C@H:8]3[C@H:17]([CH2:18][C@H:5]2[CH2:4][CH2:3]1)[C@@H:16]1[C:11](=[CH:12][C:13](=[O:19])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3>N1C=CC=CC=1.[Pd]>[OH:1][C@H:2]1[C@:6]2([CH3:20])[CH2:7][C@H:8]3[C@H:17]([CH2:18][C@H:5]2[CH2:4][CH2:3]1)[C@@H:16]1[C@@H:11]([CH2:12][C:13](=[O:19])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3

Participants

4

Reactant 1

HCID 90388059HCID 90388059, compound

Product 1

HCID 90388303HCID 90388303, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

To compound 36 (120 mg, 0.44 mmol) in pyridine (40 mL) was added Pd/C (100 mg) at room temperature. Hydrogenation was carried out under 60 psi H2. After 3 h, the pressure was released and the mixture 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 25% EtOAc in hexanes) to give compound 53 (120 mg, 4aR:4aS ratio 2.5:1): 1H NMR (CDCl3) 4aR diastereoisomer δ 3.66 (t, J=8.5 Hz, 1H), 2.58 (t, J=14.0 Hz, 1H), 2.24-0.79 (m, 23H), 0.72 (s, 3H); 13C NMR (CDCl3) δ 213.2, 81.8, 45.3, 44.8, 43.3, 43.0, 40.2, 38.8, 38.6, 36.7, 31.1, 30.4, 29.1, 29.0, 27.4, 25.7, 11.4.

Workup

  1. filtrationthe mixture 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 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-735dffaeb70b44dc95e27942237b3034
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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