Water → 1,1-Dimethylethyl (3R)-3-(2-ethoxy-2-oxoethoxy)-1-pyrrolidinecarboxylate

HRID 522285Notes

Reaction equation

HRID 522285 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[OH-].[Na+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].O>C1COCC1.CCOC(C)=O>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][O:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1)[CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 672341371,1-Dimethylethyl (3R)-3-(2-ethoxy-2-oxoethoxy)-1-pyrrolidinecarboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of tert-butyl(3R)-3-hydroxypyrrolidine-1-carboxylate (7.0 g) in THF (30 mL) was added to a suspension of 60% sodium hydroxide (2.3 g) in THF (40 mL) under ice-cooling. At the same temperature, a THF (30 mL) solution of ethyl bromoacetate (13 mL) was added to the mixture, and the mixture was stirred overnight. After water and EtOAc were added to the reaction mixture, extraction thereof was performed using EtOAc, and the extract was washed with saturated brine. The organic layer was dried over MgSO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=99:1 to 70:30), whereby tert-butyl(3R)-3-(2-ethoxy-2-oxoethoxy)pyrrolidine-1-carboxylate (6.6 g) was obtained as an oil.

Workup

  1. temperaturecooling
  2. washthe extract was washed with saturated brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Hex:EtOAc=99:1 to 70:30)

Sources & evidence

ORD record
ord-4ecfb79904564ebfb4797311b848536b
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

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