Methanol → (1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-5-phenyl-3-[(tetrahydro-2H-pyran-2-yl)oxy]pentyl]cyclopentaneethanol
Reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C2C=CC(C([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)=CC=2)C=CC=CC=1.CO>C1(C)C=CC=CC=1>[OH:23][C@@H:24]1[CH2:32][C@H:27]([OH:28])[C@H:26]([CH2:30][CH2:29][OH:31])[C@H:25]1[CH2:33][CH2:34][C@@H:35]([O:44][CH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][O:46]1)[CH2:36][CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A 1.5 M solution of diisobutylaluminum hydride in toluene (12.6 mL, 18.9 mmol) was added dropwise to a stirred solution of a compound [9a] (2.0 g, 3.5 mmol) in toluene (60 mL) at room temperature. The mixture was stirred for 3 hour at the same temperature. Methanol (50 mL) was added dropwise to the stirred mixture at −5-+5° C. and the cooling bath was removed. The mixture was stirred for 1 hours at room temperature, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate 1:5 v/v) to obtain 1.0 g (73% yield) of the compound [12a]. 1H and 13C NMR are in agreement with the structure.
Workup
- customthe cooling bath was removed
- stirringThe mixture was stirred for 1 hours at room temperature
- filtrationfiltered
- customevaporated under reduced pressure
- customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate 1:5 v/v)
Sources & evidence
- ORD record
- ord-8800742baa6044e381dadd9c802ac791
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06927300B2
Reaction notes
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