Benzyl chloroformate → Benzyl 3-bromopropylcarbamate

HRID 36182

Reaction equation

HRID 36182 reaction equation
Br.[Br:2][CH2:3][CH2:4][CH2:5][NH2:6].Cl[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].C(N(C(C)C)CC)(C)C>C1COCC1>[CH2:11]([O:10][C:8]([NH:6][CH2:5][CH2:4][CH2:3][Br:2])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 787013-Bromopropylamine hydrobromideHCID 81531Diisopropylethylamine

Product 1

HCID 254436Benzyl 3-bromopropylcarbamateYield 62.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 3-bromopropylamine hydrobromide (2 g, 9.14 mM) in 40 mL dry THF was added, via hypodermic syringe, benzyl chloroformate (1.64 g, 9.60 mM) at room temperature. After cooling to 0° C., diisopropylethylamine (1.6 mL, 9.20 mM) was added dropwise via syringe and the reaction mixture was allowed to stir at 0° C. for 1 hour. The crude reaction mixture was filtered over a pad of Celite and solvents were evaporated. The residue was flash chromatographed on silica gel, eluting with 10-20-30% EtOAc/hexane to afford 1.56 g desired product as a liquid, homogeneous by TLC in 80:20 hexane-EtOAc;

Workup

  1. additionwas added, via hypodermic syringe
  2. customat room temperature
  3. customThe crude reaction mixture
  4. filtrationwas filtered over a pad of Celite and solvents
  5. customwere evaporated
  6. customchromatographed on silica gel
  7. washeluting with 10-20-30% EtOAc/hexane

Sources & evidence

ORD record
ord-e1b2cbc13a4d4e269a66fa91b9949ec9
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

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