Sodium Sulfite → ((R)-2-Hydroxy-4-oxo-butyl)-carbamic Acid benzyl ester

HRID 1096293Notes

Reaction equation

HRID 1096293 reaction equation
[CH2:1]([O:8][C:9](=[O:17])[NH:10][CH2:11][C@H:12]([OH:16])[CH2:13][CH:14]=C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:22]CC1.I([O-])(=O)(=O)=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>CC(C)=O.C1COCC1.O.[Os](=O)(=O)(=O)=O>[CH2:1]([O:8][C:9](=[O:17])[NH:10][CH2:11][C@H:12]([OH:16])[CH2:13][CH:14]=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 66783125((R)-2-Hydroxy-pent-4-enyl)-carbamic Acid benzyl ester

Product 1

HCID 86638392((R)-2-Hydroxy-4-oxo-butyl)-carbamic Acid benzyl esterYield 133%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 21553975Acetone water tetrahydrofuranSolvent

Procedure

A mixture of ((R)-2-hydroxy-pent-4-enyl)-carbamic acid benzyl ester (690 mg, 2.35 mmol), osmium(VIII) oxide (4% solution in water, 0.22 mL, 35 μmol), and 4-methyl-morpholine-4-oxide (50% solution in water, 0.27 mL, 1.29 mmol) in acetone/THF/water 6:2:1 (6 mL) was stirred for 45 min at RT, then sodium metaperiodate (1.51 g, 7.04 mmol) was added, then after 16 h 10% aq. sodium sulfite solution (5.5 mL) was added. The reaction mixture was partitioned between EtOAc and water, the organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane-EtOAc gradient) produced the title compound (407 mg, 73%) as a brown gum.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-65826cdb9b344186a7cc0f84e8f39e26
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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