Ethyl Acetate → (3aR,4R,5R,6aS)-Hexahydro-5-(p-phenylbenzoyloxy)-4-[(3R)-5-phenyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]pentyl]-2H-cyclopenta[b]furan-2-one

HRID 584881Notes

Reaction equation

HRID 584881 reaction equation
[C:1]1([C:7]2[CH:42]=[CH:41][C:10]([C:11]([O:13][C@@H:14]3[CH2:22][C@@H:17]4[O:18][C:19](=[O:21])[CH2:20][C@@H:16]4[C@H:15]3/[CH:23]=[CH:24]/[C@@H:25]([O:34][CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][O:36]3)[CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OCC)(=O)C>[Pd].CC#N>[C:1]1([C:7]2[CH:42]=[CH:41][C:10]([C:11]([O:13][C@@H:14]3[CH2:22][C@@H:17]4[O:18][C:19](=[O:21])[CH2:20][C@@H:16]4[C@H:15]3[CH2:23][CH2:24][C@@H:25]([O:34][CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][O:36]3)[CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:12])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 10188059(3aR,4R,5R,6aS)-Hexahydro-5-(p-phenylbenzoyloxy)-4-[(3S)-5-phenyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]-1E-pentenyl]-2H-cyclopenta[b]furan-2-one

Product 1

HCID 10281424(3aR,4R,5R,6aS)-Hexahydro-5-(p-phenylbenzoyloxy)-4-[(3R)-5-phenyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]pentyl]-2H-cyclopenta[b]furan-2-oneYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of a compound [7a] (80.0 g), palladium on carbon catalyst (16 g) and ethyl acetate (1.0 L) was stirred under hydrogen atmosphere at 150 psi for 3 hours at room temperature. The reaction mixture was then filtered and evaporated under reduced pressure. The oily residue was crystallized from a mixture of hexane and ethyl acetate 4:1 v/v to give 71.4 g (89% yield) of compound [9a], mp 103-105° C., [α]D20 −107° (c 1.0, MeCN). 1H NMR (CDCl3) δ: 8.03 (d, J=8 Hz, 2H); 7.60-7.67 (m, 4H); 7.36-7.48 (m, 3H); 7.14-7.24 (m, 5H); 5.20-5.30 (m, 1H); 5.00-5.15 (m, 1H); 4.50-4.70 (m, 1H), 3.89-3.95 (m, 1H); 3.66-3.72 (m, 1H); 3.45-3.50 (m, 1H). 13C NMR (CDCl3) δ: 20.1; 25.4; 28.7; 31.3; 31.9; 36.5; 43.5; 52.8; 63.0; 76.0; 80.1; 84.3; 97.8; 125.7; 127.1; 127.2; 128.1; 128.3; 128.4; 128.9; 130.1; 140.0; 142.4; 146.0; 165.8; 176.7. IR (KBr): 2990; 1771; 1707; 1608; 1277; 1181; 1110; 1026; 751; 698 cm−1.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customevaporated under reduced pressure
  3. customThe oily residue was crystallized from a mixture of hexane and ethyl acetate 4:1 v/v

Sources & evidence

ORD record
ord-75d19743ff40425ea1c9a81c47a5c35f
Source dataset
uspto-grants-2005_08
Patent number
US06927300B2

Reaction notes

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