N-bromobutanimide → Tert-butyl 4-(5-bromo-1,3-thiazol-2-yl)piperidine-1-carboxylate

HRID 253983Notes

Reaction equation

HRID 253983 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.C1C(=O)N([Br:26])C(=O)C1>C(#N)C>[Br:26][C:5]1[S:1][C:2]([CH:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]2)=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58179889Tert-butyl 4-(thiazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 58180056Tert-butyl 4-(5-bromo-1,3-thiazol-2-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl 4-(thiazol-2-yl)piperidine-1-carboxylate (530 mg, 1.97 mmol) in acetonitrile (10 mL) was added NBS (1.40 g, 7.86 mmol). The mixture was stirred at RT for 14 hours and heated at 50° C. for 4 hours. The reaction mixture with some starting material recovered was poured into a solution of Na2SO3 (30 mL) and 6N NaOH (2 mL). The aqueous layer was extracted with EtOAc, dried over MgSO4, and the combined organics concentrated in vacuo. The residue was purified by silica gel chromatography to provide tert-butyl 4-(5-bromothiazol-2-yl)piperidine-1-carboxylate as a yellow oil [210 mg (0.61 mmol); 1H NMR (300 MHz, CDCl3) 7.59 (s, 1H), 4.20 (brd, J=12.9 Hz, 2H), 3.13 (tt, J=3.8, 11.5 Hz, 1H), 2.89 (t, J=11.6 Hz, 2H), 2.08 (d, J=11.7 Hz, 2H), 1.72 (dq, J=4.3, 11.9 Hz, 2H), 1.49 (s, 9H)].

Workup

  1. temperatureheated at 50° C. for 4 hours
  2. customThe reaction mixture with some starting material recovered
  3. additionwas poured into a solution of Na2SO3 (30 mL) and 6N NaOH (2 mL)
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialdried over MgSO4
  6. concentrationthe combined organics concentrated in vacuo
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d469ebb696bb4c5b9fda6e7c1e15074e
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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