Sodium Carbonate → (r)-2-(Hydroxyimino-methyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2243876Notes

Reaction equation

HRID 2243876 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]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].Cl.[NH2:23][OH:24]>CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[CH:14]=[N:23][OH:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 10703805tert-butyl (2R)-2-formylpiperidine-1-carboxylate

Product 1

HCID 87452998(r)-2-(Hydroxyimino-methyl)-piperidine-1-carboxylic acid tert-butyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To the title compound of Example 2.1 (3.0 g, 14.1 mmol) in MeOH/H2O (30 mL/30 mL) in an ice-bath was added Na2CO3 (895 mg, 8.4 mmol) and hydroxylamine hydrochloride (1.2 g, 16.9 mmol). After stirring for 30 minutes, the reaction mixture was warmed to room temperature and stirred for an additional 4 hours. The reaction mixture was concentrated to half volume and then extracted with ethyl acetate (2 times), washed with saturated brine, dried over anhydrous Na2SO4, filtered and concentrated to give the title product as a colorless oil (3.1 g, 97%).

Workup

  1. stirringstirred for an additional 4 hours
  2. concentrationThe reaction mixture was concentrated to half volume
  3. extractionextracted with ethyl acetate (2 times)
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-91ab9f04dbab4a54b7a977119c9c8040
Source dataset
uspto-grants-2010_03
Patent number
US07678796B2

Reaction notes

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