Hydrogen Peroxide → (S)-tert-Butyl 4-((R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxypentyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 218417Notes

Reaction equation

HRID 218417 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([CH2:26][CH:27]=[CH2:28])[CH2:11][C@H:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-:29].[Na+].OO>C1COCC1.C(OCC)C>[Si:1]([O:8][CH2:9][C@H:10]([CH2:26][CH2:27][CH2:28][OH:29])[CH2:11][C@H:12]1[CH2:16][O:15][C:14]([CH3:17])([CH3:18])[N:13]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 58011479(S)-tert-Butyl 4-((R)-2-(((tert-butyldimethylsilyl)oxy)methyl)pent-4-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 58011529(S)-tert-Butyl 4-((R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxypentyl)-2,2-dimethyloxazolidine-3-carboxylateYield 72%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-tert-butyl 4-((R)-2-((tert-butyldimethylsilyloxy)methyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate (26 g, 63 mmol) in THF (200 mL) was cooled in an ice-bath, followed by dropwise addition of 10 M BH3SMe2 (6.3 mL). After stirring for 5 hr, 10% NaOH solution (32 mL) followed by 30% H2O2 (32 mL) were added carefully. The reaction mixture was stirred at rt for 16 hr. The reaction mixture was diluted with diethyl ether (500 mL) and the aqueous layer was extracted with diethyl ether (3×250 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by column chromatography to afford (S)-tert-butyl 4-((R)-2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxypentyl)-2,2-dimethyloxazolidine-3-carboxylate (19.6 g, 72%).

Workup

  1. additionfollowed by dropwise addition of 10 M
  2. additionwere added carefully
  3. stirringThe reaction mixture was stirred at rt for 16 hr
  4. extractionthe aqueous layer was extracted with diethyl ether (3×250 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude product, which
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-badf4635cee4474ebbf222846a109c8f
Source dataset
uspto-grants-2012_06
Patent number
US08198453B2

Reaction notes

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