Sodium Bicarbonate → HCID 117777373, compound

HRID 520302Notes

Reaction equation

HRID 520302 reaction equation
[CH3:1][C:2]1([CH3:22])[C:6](=[O:7])[N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1.C(=O)(O)[O-].[Na+]>C1COCC1>[OH:7][CH:6]1[N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3][C:2]1([CH3:22])[CH3:1]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 22235302HCID 22235302, compound

Product 1

HCID 117777373HCID 117777373, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Et3BHLi (134 mL, 134 mmol, 1M in THF) was added slowly to a mixture of 137c (35 g, 112 mmol) in THF (1 L) at −78° C. and stirred for 2 h. See FIG. 1. Saturated aqueous sodium bicarbonate solution (500 mL) was added, stirred for 30 min, then extracted with DCM (1 L×3). The combined organic extracts were washed with brine (1 L×3), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give di-tert-butyl 5-hydroxy-4,4-dimethylpyrrolidine-1,2-dicarboxylate 137d as a colorless oil (38 g, crude).

Workup

  1. stirringstirred for 30 min
  2. extractionextracted with DCM (1 L×3)
  3. washThe combined organic extracts were washed with brine (1 L×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-16a0ee398f064e169779dcbf380e0c14
Source dataset
uspto-grants-2016_05
Patent number
US09326985B2

Reaction notes

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