N-methylhydroxylamine hydrochloride → HCID 59710395, compound

HRID 2221018Notes

Reaction equation

HRID 2221018 reaction equation
[CH3:1][CH:2]1[C:7](=O)[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.Cl.C[NH:18][OH:19].[C:20](=O)([O-])O.[Na+]>C1COCC1.O>[CH3:1][CH:2]1[CH2:3][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6]/[C:7]/1=[N:18]\[O:19][CH3:20]

Participants

6

Reactant 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 516892Sodium BicarbonateHCID 22644642tert-Butyl 3-methyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 59710395HCID 59710395, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,1-dimethylethyl 3-methyl-4-oxo-1-piperidinecarboxylate (367 mg, 1.72 mmol) in THF (10 mL) was treated with methylhydroxylamine hydrochloride (503 mg, 6.02 mmol) followed by a solution of sodium hydrogencarbonate (506 mg, 6.02 mmol) in water (3 mL). The reaction was stirred vigorously overnight. The reaction was then filtered, diluted with water, and extracted with dichloromethane. The crude material was purified by column chromatography (0-10% ethyl acetate/hexanes) to provide 197 mg of the desired product as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.1 (d, J=6.8 Hz, 3 H) 1.5 (s, 9 H) 2.5 (m, 1 H) 2.6 (m, 2 H) 3.5 (m, 4 H) 3.8 (s, 3 H).

Workup

  1. filtrationThe reaction was then filtered
  2. additiondiluted with water
  3. extractionextracted with dichloromethane
  4. customThe crude material was purified by column chromatography (0-10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7165f7846a2e4d93a293079c08225258
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

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