Methanol → (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-ol

HRID 584882Notes

Reaction equation

HRID 584882 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]1([C:17]2[CH:52]=[CH:51][C:20]([C:21]([O:23][C@@H:24]3[CH2:32][C@@H:27]4[O:28][C:29](=[O:31])[CH2:30][C@@H:26]4[C@H:25]3[CH2:33][CH2:34][C@@H:35]([O:44][CH:45]3[CH2:50][CH2:49][CH2:48][CH2:47][O:46]3)[CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:22])=[CH:19][CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC(C)=O.C(=O)=O.CO>C1(C)C=CC=CC=1>[C:11]1([C:17]2[CH:52]=[CH:51][C:20]([C:21]([O:23][C@@H:24]3[CH2:32][C@@H:27]4[O:28][CH:29]([OH:31])[CH2:30][C@@H:26]4[C@H:25]3[CH2:33][CH2:34][C@@H:35]([O:44][CH:45]3[CH2:50][CH2:49][CH2:48][CH2:47][O:46]3)[CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:22])=[CH:19][CH:18]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 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-oneHCID 18522661Acetone cardiceHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 11180616(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-olYield 49%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 1.5 M solution of diisobutylaluminum hydride in toluene (6.0 mL, 9.0 mmol) was added dropwise to a stirred solution of compound [9a] (4.1 g, 7.2 mmol) in toluene (60 mL) at −70-−80° C. (acetone/dry ice bath) and the resulting mixture was stirred during 1 h at the same temperature. Methanol (10 mL) was added dropwise to the stirred mixture at −70-−80° C. The mixture was stirred for 1 hour at room temperature, filtered and evaporated under reduced pressure. Dichloromethane (30 mL) was added to the residue. The resulting solution was washed with brine (2×10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate 2:1 v/v) to obtain 2.0 g (49% yield) of the compound [10a]. 1H NMR (CDCl3) δ: 6.4-6.5 (m, 1H); 5.0-5.2 (m, 1H); 4.7-4.9 (m, 1H); 4.5-4.7 (m, 1H); 3.8-4.0 (m, 1H); 3.6-3.8 (m, 1H); 3.4-3.6 (m, 1H). 13C NMR (CDCl3) δ: 20.1; 25.5; 28.6; 31.3; 31.6; 36.7; 37.7; 40.3; 41.1; 46.2; 51.6; 63.0; 81.3; 82.0; 97.8; 100.2; 125.6; 127.1; 127.2; 128.1; 128.3; 128.4; 128.9; 129.2; 130.0; 130.1; 140.0; 145.7; 166.0. IR (KBr): 3500, 2945, 1712, 1605, 1278, 1117, 1026, 752 cm−1.

Workup

  1. stirringThe mixture was stirred for 1 hour at room temperature
  2. filtrationfiltered
  3. customevaporated under reduced pressure
  4. additionDichloromethane (30 mL) was added to the residue
  5. washThe resulting solution was washed with brine (2×10 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate 2:1 v/v)

Sources & evidence

ORD record
ord-464c058e38244e64b8eed3d6e84e676e
Source dataset
uspto-grants-2005_08
Patent number
US06927300B2

Reaction notes

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