N-bromobutanimide → 1-tert-Butyloxycarbonyl-3-bromo-4-oxopiperidine

HRID 1634201Notes

Reaction equation

HRID 1634201 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH:20]=[C:19]([O:22][Si](C)(C)C)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>C(#N)C.C(OCC)(=O)C>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH:18]([Br:8])[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 10778540tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 106839701-tert-Butyloxycarbonyl-3-bromo-4-oxopiperidineYield 87.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

NBS (1.4 g) was added to a solution of 1-tert-butoxycarbonyl-1,2,3,6-tetrahydro-4-(trimethylsilyloxy)pyridine (2 g) in acetonitrile and the mixture was stirred at room temperature for 30 minutes. The solution was diluted with ethyl acetate(50 ml) and washed with water (50 ml), sodium bicarbonate solution (50 ml) and brine (50 ml), dried (MgSO4) and evaporated to give the title compound as a colourless solid (1.8 g).

Workup

  1. washwashed with water (50 ml), sodium bicarbonate solution (50 ml) and brine (50 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-9e50011067924b0aa3bd679630e21393
Source dataset
uspto-grants-2003_01
Patent number
US06506773B2

Reaction notes

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