Potassium Hydroxide → HCID 86703443, compound

HRID 245596Notes

Reaction equation

HRID 245596 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH2:17][C@@H:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C@H:15](/[CH:26]=[CH:27]/[C@@H:28]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C@H:14]2[CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([O:49]CC3C=CC=CC=3)[CH:44]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[K+]>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH2:17][C@@H:16]([O:18][Si:19]([C:22]([CH3:23])([CH3:24])[CH3:25])([CH3:21])[CH3:20])[C@H:15](/[CH:26]=[CH:27]/[C@@H:28]([O:34][Si:35]([C:38]([CH3:39])([CH3:40])[CH3:41])([CH3:36])[CH3:37])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C@H:14]2[CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([OH:49])[CH:44]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86677379((1S,2S,3R,4R)-2-(3-(benzyloxy)benzyl)-4-(tert-butyldimethylsilyoxy)-3-((S,E)-3-(tert-butyldimethylsilyoxy)oct-1-enyl)cyclopentyl)methyl 4-methylbenzenesulfonate

Product 1

HCID 86703443HCID 86703443, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ((1S,2S,3R,4R)-2-(3-(benzyloxy)benzyl)-4-(tert-butyldimethylsilyoxy)-3-((S,E)-3-(tert-butyldimethylsilyoxy)oct-1-enyl)cyclopentyl)methyl 4-methylbenzenesulfonate (15.7 g, 0.019 mol) in dry methanol (150 ml) was treated with potassium hydroxide (3.25 g, 0.057 mol), then with 5% Pd/C (6.28 g, 40% wt) under hydrogen for 5 hr. Then, the reaction mixture was filtered with celite pad. The solvent was evaporated off under vacuum. The crude product was purified by chromatography on silica gel using a mixture of hexane and ethyl acetate as a gradient eluent. Yield: 90%

Workup

  1. filtrationThen, the reaction mixture was filtered with celite pad
  2. customThe solvent was evaporated off under vacuum
  3. customThe crude product was purified by chromatography on silica gel using
  4. additiona mixture of hexane and ethyl acetate as a gradient eluent

Sources & evidence

ORD record
ord-cb745089f54340fa814c5612634f551a
Source dataset
uspto-grants-2014_02
Patent number
US08658837B2

Reaction notes

Loading…