Chlorosuccinimide → HCID 86644157, compound

HRID 534085Notes

Reaction equation

HRID 534085 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 fraction 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-97b5b5b130a3473a8dceb7b5f9319f8f
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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