Sodium hydride → HCID 67033996, compound

HRID 539068Notes

Reaction equation

HRID 539068 reaction equation
[CH:1]1([CH2:4][C@H:5]([NH:8][C:9](=[O:18])[O:10][CH2:11]C2C=CC=CC=2)CO)[CH2:3][CH2:2]1.[H-].[Na+]>CN(C=O)C>[CH:1]1([CH2:4][C@H:5]2[CH2:11][O:10][C:9](=[O:18])[NH:8]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86667829HCID 86667829, compound

Product 1

HCID 67033996HCID 67033996, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (S)-benzyl 1-cyclopropyl-3-hydroxypropan-2-ylcarbamate (0.734 g, 2.94 mmol) in DMF (15 mL) was added sodium hydride (0.177 g, 4.42 mmol) at 0° C. The mixture was then stirred at ambient temperature for 30 minutes. The solvent was concentrated and the residue distributed between water and EtOAc. The combined organic extracts were dried (phase separator silicone treated filter paper), concentrated to provide (S)-4-(cyclopropylmethyl)oxazolidin-2-one (0.318 g, 76% yield) as a clear oil.

Workup

  1. concentrationThe solvent was concentrated
  2. customThe combined organic extracts were dried
  3. addition(phase separator silicone treated filter paper)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1d44b7bc0566424aba5cccf148f690bd
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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