Water → (R)-N-hydroxy-2,2,5,5-tetramethyl-1,3-dioxolane-4-carbimidoyl chloride

HRID 1511114Notes

Reaction equation

HRID 1511114 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]([CH:7]=[N:8][OH:9])[C:4]([CH3:11])([CH3:10])[O:3]1.[Cl:13]N1C(=O)CCC1=O.O>CN(C=O)C>[OH:9][N:8]=[C:7]([Cl:13])[C@H:5]1[C:4]([CH3:11])([CH3:10])[O:3][C:2]([CH3:12])([CH3:1])[O:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 86644152(S)-2,2,5,5-tetramethyl-1,3-dioxolane-4-carbaldehyde oxime

Product 1

HCID 86644153(R)-N-hydroxy-2,2,5,5-tetramethyl-1,3-dioxolane-4-carbimidoyl chlorideYield 79.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-2,2,5,5-tetramethyl-1,3-dioxolane-4-carbaldehyde oxime (13 g, 75.1 mmol) was dissolved in DMF (200 mL) and cooled in an ice bath. 1-Chloropyrrolidine-2,5-dione (10.0 g, 75.1 mmol) was added and the reaction was stirred overnight, slowly warming to ambient temperature. The pale yellow solution was poured into water (1.5 L) and extracted with EtOAc. The combined organic layers were washed with water and brine, dried, filtered and concentrated. The residue was purified over silica gel (40% EtOAc in hexanes) to afford (R)-N-hydroxy-2,2,5,5-tetramethyl-1,3-dioxolane-4-carbimidoyl chloride (12.4 g, 59.7 mmol, 79.6% yield).

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified over silica gel (40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4a68bd0443e74470b1e6637f1eeb6933
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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