Potassium Iodide → HCID 10826398, compound

HRID 888311Notes

Reaction equation

HRID 888311 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-].[K+].[OH-].[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1(C)C=CC=CC=1.CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 14797Potassium HydroxideHCID 24477Sodium ThiosulfateHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 10826398HCID 10826398, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolvent3×

Conditions

Temperature
70 °C

Procedure

Dimethyl sulfoxide (50 g) was added to about 60% toluene solution of N-tert-butoxycarbonyl-(R)-3-hydroxypyrrolidine (20 g) which had been obtained separately, and potassium iodide (5.32 g) and a solid of 85% potassium hydroxide (14.1 g) were added thereto. After the slurry solution was heated to 70° C., benzyl chloride (17.58 g) was dropped for 5 hours. Subsequently, after the solution was stirred for 16 hours, a conversion rate (*) reached 98%. After the reaction finished, the solution was cooled to 20° C., and toluene and 30% aqueous solution of sodium thiosulfate were added and an aqueous layer was removed, followed by washing an organic layer with water. The resultant organic layer was concentrated under reduced pressure, thereby obtaining toluene solution of N-tert-butoxycarbonyl-(R)-3-benzyloxypyrrolidine (yield: 98%). (*) Conversion rate (%)=(amount of production of N-tert-butoxycarbonyl-(R)-3-benzyloxypyrrolidine g))/[(amount of production of N-tert-butoxycarbonyl-(R)-3-benzyloxypyrrolidine g))+(residual amount of N-tert-butoxycarbonyl-(R)-3-hydroxypyrrolidine(g))]

Workup

  1. customhad been obtained separately
  2. temperaturethe solution was cooled to 20° C.
  3. customan aqueous layer was removed
  4. washby washing an organic layer with water
  5. concentrationThe resultant organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3dd82ad6fe0746a6853c8ce3e50dafb6
Source dataset
uspto-grants-2012_08
Patent number
US08247578B2

Reaction notes

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