Chlorosuccinimide → HCID 86644157, compound

HRID 1511105Notes

Reaction equation

HRID 1511105 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[O:8][C:7]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[O:6][CH:5]1[CH:14]=[N:15][OH:16].[Cl:17]N1C(=O)CCC1=O>CN(C=O)C>[OH:16][N:15]=[C:14]([Cl:17])[C@H:5]1[C@H:4]([CH2:3][O:2][CH3:1])[O:8][C:7]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[O:6]1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86644156HCID 86644156, compound

Product 1

HCID 86644157HCID 86644157, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(Methoxymethyl)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde oxime (33.2 g, 145 mmol) was dissolved in DMF (600 mL) and cooled in an ice bath. 1-Chloropyrrolidine-2,5-dione (19.3 g, 145 mmol) was added and the reaction allowed to slowly warm to ambient temperature overnight. Most of the DMF was removed under reduced pressure and the remaining material was partitioned between water and EtOAc. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated to afford (2R,3S)-N-hydroxy-3-(methoxymethyl)-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride (35.6 g, 135 mmol, 93.2% yield) which was taken forward without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. customMost of the DMF was removed under reduced pressure
  3. customthe remaining material was partitioned between water and EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7e56673ce43f453db0434e22aedf264e
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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