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Hydrogen Peroxide → 4-(3-{3-(Tert-butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-hydroxy-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl ester

HRID 1393696
Notes
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Reaction equation

HRID 1393696 reaction equation
[CH3:1][O:2][C:3](=[O:48])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]2[C:17](=[O:18])[CH2:16][CH:15]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:14]2[CH:27]=[CH:28][CH:29]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH:30]([CH3:35])[CH2:31][C:32]#[C:33][CH3:34])[C:8]=1[O:44][CH2:45][O:46][CH3:47].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].OO>C1COCC1>[CH3:1][O:2][C:3](=[O:48])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]2[CH:17]([OH:18])[CH2:16][CH:15]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH:14]2[CH:27]=[CH:28][CH:29]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH:30]([CH3:35])[CH2:31][C:32]#[C:33][CH3:34])[C:8]=1[O:44][CH2:45][O:46][CH3:47]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 69215476HCID 69215476, compound

Product 1

HCID 692154174-(3-{3-(Tert-butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-hydroxy-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-(3-{3-(tert-Butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-oxo-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl ester of 2.6 g (3.67 mmol) was dissolved in THF (40 ml). The solution was cooled to −78° C., and then, L-selectride (1 M.THF solution, 7.35 mmol) was slowly added thereto dropwise. The mixture was stirred at the above temperature for 2 hours, and the reaction was stopped with hydrogen peroxide (30% aqueous solution, 16 mmol). The reaction solution was stirred at 0° C. for 30 minutes, and then, extracted with diethyl ether. The combined organic layer was washed with water and brine, and then, dried over magnesium sulfate, filtered off, and concentrated under reduced pressure. The concentrate was subjected to column chromatography on a silica gel (hexane:ethyl acetate=4:1) to obtain 4-(3-{3-(tert-butyl-dimethyl-silanyloxy)-2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-oct-1-en-6-ynyl]-5-hydroxy-cyclopentyl}-2-methoxymethoxy-phenyl)-butyric acid methyl ester (2.3 g, yield: 90%).

Workup

  1. stirringThe reaction solution was stirred at 0° C. for 30 minutes
  2. extractionextracted with diethyl ether
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0aceb9f746ab4c28907b3a584e16b1f9
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07345181B2

Reaction notes

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