Benzyl chloroformate → Benzyl prop-2-yn-1-ylcarbamate

HRID 2300557Notes

Reaction equation

HRID 2300557 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].[CH2:5]([O:12][C:13](Cl)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>N1C=CC=CC=1.C(Cl)Cl>[CH2:5]([O:12][C:13](=[O:14])[NH:4][CH2:1][C:2]#[CH:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 239041Propargylamine

Product 1

HCID 11137906Benzyl prop-2-yn-1-ylcarbamateYield 32.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of propargylamine (6.4 g, 71.2 mmol) in pyridine (100 mL) was added benzylchloroformate (13.37 g, 78.2 mmol) in 10 mL CH2Cl2 over 0.5 h. The reaction was stirred for 16 h and the volatiles were removed in vacuo. The residue was dissolved in EtOAc and the organic solution was washed with water (2×). The organic solution was washed with dilute aqueous HCl followed by saturated NaHCO3. The organic solution was dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound of Step A (4.43 g).

Workup

  1. customthe volatiles were removed in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washthe organic solution was washed with water (2×)
  4. washThe organic solution was washed with dilute aqueous HCl
  5. dry with materialThe organic solution was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3acc9ada00dd46ba806f5531f8646b8f
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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