Sodium hydride → HCID 72330455, compound

HRID 2206944Notes

Reaction equation

HRID 2206944 reaction equation
[OH:1][CH:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1.[H-].[Na+].[S:20]([O:30][CH2:31][CH2:32]OS(C1C=CC(C)=CC=1)(=O)=O)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>CN(C=O)C>[C:26]1([CH3:27])[CH:25]=[CH:24][C:23]([S:20]([O:30][CH2:31][CH2:32][O:1][CH:2]2[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[CH:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]2)(=[O:22])=[O:21])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 228289Ethylene glycol ditosylateHCID 51482991-Tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Product 1

HCID 72330455HCID 72330455, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 2.45 g (10.0 mmol) of 1-tert-butyl 2-methyl 4-[hydroxy]pyrrolidine-1,2-dicarboxylate (24) in DMF (10 ml) was added to a suspension of 0.65 g (15 mmol) of sodium hydride in DMF (20 ml). After 15 min, a solution of 5.56 g (15.0 mmol) of 1,2-ethanediol bistosylate in DMF (10 ml) was added. The batch was subsequently reacted in 3 portions at 100° C. in a microwave for 45 minutes. The batch was concentrated and treated with water and ethyl acetate. After phase separation, the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and the solvent was removed in vacuo. The crude product was purified by column chromatography (silica gel, hexane/ethyl acetate). 1.2 g (27%) of 1-tert-butyl 2-methyl 4-[2-(toluene-4-sulfonyloxy)ethoxy]pyrrolidine-1,2-dicarboxylate were obtained.

Workup

  1. customThe batch was subsequently reacted in 3 portions at 100° C. in a microwave for 45 minutes
  2. concentrationThe batch was concentrated
  3. additiontreated with water and ethyl acetate
  4. customAfter phase separation
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customThe crude product was purified by column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3141813e7f7a46428915f285e7d58984
Source dataset
uspto-grants-2016_06
Patent number
US09375497B2

Reaction notes

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