Sodium Thiosulfate → HCID 10779491, compound

HRID 1912439Notes

Reaction equation

HRID 1912439 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:17][CH2:18][CH2:19][OH:20])[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4].C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([CH2:17][CH2:18][CH:19]=[O:20])[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])=[O:4]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087Triacetoxyperiodinane3×HCID 516892Sodium Bicarbonate2×HCID 10589368HCID 10589368, compound

Product 1

HCID 10779491HCID 10779491, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-(3-hydroxypropyl)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (17.4 g) and sodium bicarbonate (12.7 g) in chloroform (175 ml) cooled to 0° C. was added Dess-Martin periodinane (28.3 g). The reaction mixture was warmed to room temperature and stirred for 1.5 hours. To the reaction mixture was added additional Dess-Martin periodinane (1.0 g), and the mixture was stirred for 50 minutes. To the reaction mixture cooled to 0° C. was added additional Dess-Martin periodinane (15 g), and the mixture was stirred for 2 hours. To the mixture were added 20% sodium thiosulfate (250 ml) and saturated aqueous sodium bicarbonate solution (250 ml), and the mixture was stirred at room temperature for 20 minutes. The mixture was extracted with chloroform (200 ml×2) twice, and the combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1 to 3/2) to give the titled compound (5.68 g).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringthe mixture was stirred for 50 minutes
  3. temperatureTo the reaction mixture cooled to 0° C.
  4. stirringthe mixture was stirred for 2 hours
  5. stirringthe mixture was stirred at room temperature for 20 minutes
  6. extractionThe mixture was extracted with chloroform (200 ml×2) twice
  7. dry with materialthe combined organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1 to 3/2)

Sources & evidence

ORD record
ord-c78a048c813248f6aca58349723b9f53
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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