N-bromobutanimide → tert-Butyl 4-(2-Bromoacetyl)piperidine-1-carboxylate

HRID 1804597Notes

Reaction equation

HRID 1804597 reaction equation
C[Si](C)(C)[O:3][C:4]([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)=[CH2:5].C(=O)(O)[O-].[Na+].C1C(=O)N([Br:33])C(=O)C1.[Na]>C1COCC1>[Br:33][CH2:3][C:4]([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)=[O:5]

Participants

6

Reactant 4

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 67972300Tert-butyl 4-{1-[(trimethylsilyl)oxy]vinyl}piperidine-1-carboxylate

Product 1

HCID 18187487tert-Butyl 4-(2-Bromoacetyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve the title compound from Step A above (6.0 g, 20 mmol) in THF (120 mL), cool to 0° C. and add sodium bicarbonate. To the resulting suspension was added NBS and the mixture stirred for 1.5 h. TLC showed no starting material left. Poured reaction into sat'd aqueous sodium buicarbonate solution (200 mL) and extracted with ether (2×200 mL). The organics were combined, washed with water and brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The resulting product (6.4 g, 99%) was used without further purification for the next reaction. ESI-MS calculated for C12H20BrNO3: Exact Mass: 305.06. Found: 305.15 (M)+ and 307.09 (M+2)+.

Workup

  1. waitleft
  2. additionPoured
  3. extractionextracted with ether (2×200 mL)
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe resulting product (6.4 g, 99%) was used without further purification for the next reaction

Sources & evidence

ORD record
ord-77148f9c69414423bc1f499652132c09
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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