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

HRID 1809561Notes

Reaction equation

HRID 1809561 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>CCOCC>[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 54%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 500 mL flask was charged with tert-butyl 4-(chloro(hydroxyimino)methyl)piperidine-1-carboxylate (2.3 g, 8.7 mmol), methanesulfonyl chloride (0.68 mL, 8.7 mmol), and Et2O (200 mL). Triethylamine (1.2 mL, 8.7 mmol) was added slowly over ˜1 minute and the reaction was stirred at ambient temperature for 10 minutes. The resultant precipitate was filtered and the filtrate concentrated and purified on silica (100% CH2Cl2) to afford tert-butyl 4-(chloro(methylsulfonyloxyimino)methyl)piperidine-1-carboxylate (1.6 g, 53.63% yield) as a c.c. oil.

Workup

  1. filtrationThe resultant precipitate was filtered
  2. concentrationthe filtrate concentrated
  3. custompurified on silica (100% CH2Cl2)

Sources & evidence

ORD record
ord-564c2227a08b4245bac49ca0c1b82308
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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