N-bromobutanimide → HCID 58293817, compound

HRID 446729Notes

Reaction equation

HRID 446729 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.C1C(=O)N([Br:27])C(=O)C1>C(#N)C>[Br:27][C:4]1[S:3][C:2]([CH3:1])=[C:6]([CH:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)[CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58293794HCID 58293794, compound

Product 1

HCID 58293817HCID 58293817, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of Compound 1059 (810 mg; 2.89 mmol) in 15 mL of acetonitrile was added NBS portionwise (505 mg; 2.83 mmol). The reaction mixture was stirred at room temperature for 10 minutes, quenched with saturated Na2SO3 solution, and extracted with EtOAc (3×). The combined organics were dried (Na2SO4), filtered, and concentrated in vacuo to give a crude light yellow semi-solid. The residue was purified by medium pressure silica gel chromatography, eluting with 0-20% EtOAc/hexanes over 25 minutes, to give tert-butyl 4-(5-bromo-2-methylthiophen-3-yl)piperidine-1-carboxylate (Compound 1060, 590 mg, 57%); 1H NMR (CDCl3): δ 6.7 (s, 1H), 4.2 (m, 2H), 2.6 (m, 3H), 2.2 (s, 3H), 1.6 (m, 2H), 1.5 (m, 2H), 1.45 (s, 9H).

Workup

  1. customquenched with saturated Na2SO3 solution
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a crude light yellow semi-solid
  7. customThe residue was purified by medium pressure silica gel chromatography
  8. washeluting with 0-20% EtOAc/hexanes over 25 minutes

Sources & evidence

ORD record
ord-6e5da2cd1c064ce8a1da6fc5dd2a4b97
Source dataset
uspto-grants-2013_07
Patent number
US08481524B2

Reaction notes

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