Sodium Carbonate → HCID 68910472, compound

HRID 732626Notes

Reaction equation

HRID 732626 reaction equation
C(=O)(O)O.ClC(Cl)C.C([N:16]1[CH2:20][C@H:19]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[C@@H:18]([CH2:30][O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH2:17]1)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[Si:32]([O:31][CH2:30][C@@H:18]1[C@@H:19]([C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)[CH2:20][NH:16][CH2:17]1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 68917211HCID 68917211, compoundHCID 86628528HCID 86628528, compound

Product 1

HCID 68910472HCID 68910472, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-Chloroethyl chloride carbonate was added to 4 ml of a 1,2-dichloroethane solution of 390 mg of (3R,4S)-1-benzyl-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(4-nitrophenyl)pyrrolidine under cooling with ice bath, and this was warmed up to room temperature and stirred for 2Hours. This was again cooled in an ice bath, mixed with saturated sodium carbonate aqueous solution, warmed up to room temperature and stirred for 30 minutes. This was extracted twice with chloroform, and the combined organic layer was washed with saturated brine, dried with anhydrous sodium sulfate and then concentrated under a reduced pressure. The oily residue was dissolved in 4 ml of methanol and heated under reflux for 5Hours. After concentration under a reduced pressure, the residue was purified by a silica gel column chromatography (chloroform-methanol) to obtain 290 mg of (3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(4-nitrophenyl)pyrrolidine as an orange oily substance.

Workup

  1. temperatureunder cooling with ice bath
  2. temperatureThis was again cooled in an ice bath
  3. temperaturewarmed up to room temperature
  4. stirringstirred for 30 minutes
  5. extractionThis was extracted twice with chloroform
  6. washthe combined organic layer was washed with saturated brine
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationconcentrated under a reduced pressure
  9. dissolutionThe oily residue was dissolved in 4 ml of methanol
  10. temperatureheated
  11. temperatureunder reflux for 5Hours
  12. concentrationAfter concentration under a reduced pressure
  13. customthe residue was purified by a silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-7ec16cd6bb4148f88d88ca96c71b2177
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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