Triethylamine → Tert-butyl 4-(chloro(methylsulfonyloxyimino)methyl)piperidine-1-carboxylate

HRID 1972161Notes

Reaction equation

HRID 1972161 reaction equation
[Cl:1][C:2](=[N:16][OH:17])[CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C>C(OCC)C>[Cl:1][C:2](=[N:16][O:17][S:19]([CH3:18])(=[O:21])=[O:20])[CH:3]1[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 76573117Tert-butyl 4-(chloro(hydroxyimino)methyl)piperidine-1-carboxylate

Product 1

HCID 86640985Tert-butyl 4-(chloro(methylsulfonyloxyimino)methyl)piperidine-1-carboxylateYield 53.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

tert-Butyl 4-(chloro(hydroxyimino)methyl)piperidine-1-carboxylate (2.3 g, 8.75 mmol) and methanesulfonyl chloride (0.68 mL, 8.75 mmol) were suspended in diethyl ether (200 mL). Triethylamine (1.22 mL, 8.75 mmol) was added and the reaction stirred at ambient temperature until consumption of starting material. The mixture was filtered and the filtrate was concentrated. The residue was purified by flash chromatography (using dichloromethane) to afford the title compound (1.6 g, 53% yield) as a clear oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by flash chromatography (using dichloromethane)

Sources & evidence

ORD record
ord-d5d92b4431bb4166a452e24b126685e2
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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