Chlorosuccinimide → Tert-butyl (2r)-2-[chloro(hydroxyimino)methyl]piperidine-1-carboxylate

HRID 2243877Notes

Reaction equation

HRID 2243877 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[CH:14]=[N:15][OH:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:17]N1C(=O)CCC1=O>CN(C=O)C.C(OCC)(=O)C>[Cl:17][C:14](=[N:15][OH:16])[C@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 87452998(r)-2-(Hydroxyimino-methyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 87869110Tert-butyl (2r)-2-[chloro(hydroxyimino)methyl]piperidine-1-carboxylateYield 86.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the title compound of Example 3.1 (3.1 g, 13.7 mmol) in DMF (30 mL) at 40° C. was added N-chlorosuccinimide (2.0 g, 15.1 mmol) in 3 portions. After stirring for 1 hour, the reaction mixture was diluted with ethyl acetate and then the organic layer washed with water (3 times) and brine, dried over anhydrous Na2SO4, filtered and concentrated to give the title product (3.1 g, 85%).

Workup

  1. washthe organic layer washed with water (3 times) and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9cf9ab72d39146c79ee45ad7c319c1ac
Source dataset
uspto-grants-2010_03
Patent number
US07678796B2

Reaction notes

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