Benzyl chloroformate → 3-N-Cbz-Aminomethylaniline

HRID 735674Notes

Reaction equation

HRID 735674 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>C1COCC1>[CH2:14]([O:13][C:11](=[O:12])[NH:6][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([NH2:1])[CH:3]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 46288313-Aminobenzylamine

Product 1

HCID 27573803-N-Cbz-AminomethylanilineYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-aminobenzylamine (610 mg, 5 mmol) and TEA (1.01 g, 10 mmol) in 10 mL of THF at 0° C., was added benzyl chloroformate (936 mg, 5.5 mmol) dropwise. The mixture was stirred at rt for 30 min. The reaction was quenched with water and extracted with EtOAc (3×20 mL). The organic layer was washed with brine, dried (Na2SO4) and concentrated. Purification via flash chromatography (0 to 50% EtOAc in hexanes) gives 66A (911 mg, 71%). MS (ESI) m/z 257.3 (M+H)+.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification via flash chromatography (0 to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d7bf640885b2428ea0bec99b4438b3d5
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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