Potassium Hydroxide → HCID 86677382, compound

HRID 39613Notes

Reaction equation

HRID 39613 reaction equation
[CH3:1][S:2]([O:5][CH2:6][C@H:7]1[CH2:11][C@@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[C@H:9](/[CH:20]=[CH:21]/[C@@H:22]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C@H:8]1[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([O:43]CC2C=CC=CC=2)[CH:38]=1)(=[O:4])=[O:3].[OH-].[K+]>CO.[Pd]>[CH3:1][S:2]([O:5][CH2:6][C@H:7]1[CH2:11][C@@H:10]([O:12][Si:13]([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14])[C@H:9](/[CH:20]=[CH:21]/[C@@H:22]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C@H:8]1[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([OH:43])[CH:38]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86677383((1S,2S,3R,4R)-2-(3-(benzyloxy)benzyl)-4-(tert-butydimethylsilyoxy)-3-((S,E)-3-(tert-butyldimethylsilyoxy)oct-1-enyl)cyclopentyl)methyl methanesulfonate

Product 1

HCID 86677382HCID 86677382, compoundYield 127.2%

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 methanesulfonate (45 g, 0.06 mol) in dry methanol (450 ml) was treated with potassium hydroxide (9.72 g, 0.18 mol), then with 5% Pd/C (13.5 g, 30% wt) under hydrogen for 2 hr. Then, the reaction mixture was filtered with celite pad. The filtrate was concentrated to obtain crude product (50 g).

Workup

  1. filtrationThen, the reaction mixture was filtered with celite pad
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-da3a7050e8bd4ead919af4431dbf2100
Source dataset
uspto-grants-2013_09
Patent number
US08524939B2

Reaction notes

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