Water → (R)-N-hydroxy-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride

HRID 1523539Notes

Reaction equation

HRID 1523539 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[O:4][CH2:3][C@@H:2]1[CH:11]=[N:12][OH:13].[Cl:14]N1C(=O)CCC1=O.O>CN(C=O)C>[OH:13][N:12]=[C:11]([Cl:14])[C@H:2]1[CH2:3][O:4][C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[O:1]1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 390821HCID 390821, compound

Product 1

HCID 86644146(R)-N-hydroxy-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chlorideYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde oxime (9.08 g, 49 mmol) in DMF (50 mL) was added 1-chloropyrrolidine-2,5-dione (7.20 g, 53.9 mmol) and the reaction stirred overnight at ambient temperature. The reaction was poured into water (500 mL) extracted with ether. The organics were washed with brine and dried over magnesium sulfate. The material was concentrated in vacuo to yield (R)—N-hydroxy-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride (10.4 g, 47 mmol, 96.6%).

Workup

  1. extractionextracted with ether
  2. washThe organics were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe material was concentrated in vacuo

Sources & evidence

ORD record
ord-e6108d3eeca44b7a9b97a15ceb5e3984
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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