HCID 90388545, compound → HCID 90388260, compound

HRID 2201729Notes

Reaction equation

HRID 2201729 reaction equation
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[CH2:14][C@@H:13]1[C@H:4]([CH2:5][CH2:6][C:7]3[C@H:12]1[CH2:11][CH2:10][C:9](=[O:20])[CH:8]=3)[CH2:3]2>N1C=CC=CC=1.[Pd]>[CH3:1][C@@:2]12[C:18](=[O:19])[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@H:12]1[CH2:11][CH2:10][C:9](=[O:20])[CH2:8]3)[CH2:3]2

Participants

4

Reactant 1

HCID 90388545HCID 90388545, compound

Product 1

HCID 90388260HCID 90388260, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

To a solution compound 12 (150 mg, 0.54 mmol) in pyridine (30 mL) was added Pd/C (50 mg) at room temperature. A hydrogenation was carried out under 7 atm H2 for 2 h at room temperature. The reaction was filtered through Celite® 545 which was washed with EtOAc (100 mL). Solvents were removed under reduced pressure and 13C NMR of the crude product (145 mg) showed the 4aS to 4aR diastereomer ratio to be 2:1: 1H NMR (CDCl3) δ 0.84 (s, 3H); 13C NMR (CDCl3) 4aS diastereomer δ 220.4, 212.2, 47.8, 45.6, 42.7, 39.9, 38.9, 38.6, 38.2, 38.1, 36.3, 35.4, 30.7, 28.5, 28.4, 27.1, 23.9, 13.5.

Workup

  1. filtrationThe reaction was filtered through Celite® 545 which
  2. washwas washed with EtOAc (100 mL)
  3. customSolvents were removed under reduced pressure and 13C NMR of the crude product (145 mg)

Sources & evidence

ORD record
ord-af4b2738d5f747559016846681d15bef
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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