Sodium Bicarbonate → 4-Methoxyimino-piperidine-1-carboxylic Acid Tert-butyl Ester

HRID 1864498Notes

Reaction equation

HRID 1864498 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.Cl.[O:16]([NH2:18])[CH3:17].C(=O)(O)[O-].[Na+]>C1COCC1.O>[C:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][C:2](=[N:18][O:16][CH3:17])[CH2:3][CH2:4]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 497591414-Methoxyimino-piperidine-1-carboxylic Acid Tert-butyl EsterYield 92.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 4-oxo-1-piperidinecarboxylate (2.0 g) and methoxylamine hydrochloride (2.93 g) in THF (66 mL) was treated with sodium bicarbonate (2.95 g) dissolved in water (20 mL). The biphasic mixture was stirred vigorously for 10 minutes, diluted with water, and extracted with ethyl acetate (×3). The combined extracts were dried over magnesium sulfate, filtered and concentrated to afford 2.12 g of the title compound, which was used without further purification. 1H NMR (CDCl3, 300 MHz) δ ppm 1.49 (s, 9H), 2.34 (t, 2H, J=6.07 Hz), 2.57 (t, 2H, J=6.07 Hz), 3.51 (t, 2H, J=6.07 Hz), 3.56 (t, 2H, J=6.07 Hz), 3.85 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6e6b1dfac8a7489fbb882c4faad74dc7
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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