Reaction equation
[OH:1][C@H:2]1[C@H:18]([CH2:19][CH2:20][C@@H:21]([OH:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C@H:5]2[CH2:6][C:7]3[C:12]([CH2:13][C@H:4]2[CH2:3]1)=[C:11]([O:14][CH2:15][C:16]#N)[CH:10]=[CH:9][CH:8]=3.[OH-:28].[K+].Cl.C[OH:32]>>[CH3:26][CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]([OH:27])[CH2:20][CH2:19][C@H:18]1[C@H:2]([OH:1])[CH2:3][C@H:4]2[C@@H:5]1[CH2:6][C:7]1[C:12]([CH2:13]2)=[C:11]([O:14][CH2:15][C:16]([OH:32])=[O:28])[CH:10]=[CH:9][CH:8]=1Participants
Conditions
- Temperature
- 10 °C
Procedure
2-((1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yloxy)acetonitrile (2 g, 0.05 mol) in methanol (18 ml) was treated with 20% KOH (6 ml) and refluxed for 3 hr. The reaction was then cooled to 10° C. and 3N HCl was added slowly until pH=˜8. The solvent was removed in vacuo. Ethyl acetate and brine were added and then 3N HCl was added slowly until pH=2. The reaction mixture was extracted with ethyl acetate. The combined ethyl acetate extracts were dried over anhydrous magnesium sulfate. The solid was filtered off. The solvent was evaporated off under vacuum. The crude product was purified by crystallization from ethanol/H2O. The titled compound was obtained in a crystalline form. Yield: 81%.
Workup
- temperaturerefluxed for 3 hr
- customThe solvent was removed in vacuo
- additionEthyl acetate and brine were added
- addition3N HCl was added slowly until pH=2
- extractionThe reaction mixture was extracted with ethyl acetate
- dry with materialThe combined ethyl acetate extracts were dried over anhydrous magnesium sulfate
- filtrationThe solid was filtered off
- customThe solvent was evaporated off under vacuum
- customThe crude product was purified by crystallization from ethanol/H2O
Sources & evidence
- ORD record
- ord-56ec96b01565429a87d2fb3bc9825319
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658837B2
Linked notes
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