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

HRID 1809474Notes

Reaction equation

HRID 1809474 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].C(N(CC)CC)C.Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>C(Cl)Cl>[CH2:1]([NH:4][C:13](=[O:14])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 239041Propargylamine

Product 1

HCID 11137906Benzyl prop-2-yn-1-ylcarbamateYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of propargylamine and triethylamine (1.3 eq.) in DCM (3 M) at 0° C., it was added dropwise a solution of benzyl chloroformate (1.1 eq.) in DCM (5 M). The reaction mixture was stirred at RT for 2 h. After evaporation of the solvent the resulting residue was purified by flash column chromatography on silica (EtOAc/Petroleum ether 1:10) to yield (56%) the title compound. 1H NMR (300 MHz, CDCl3, 300K) δ 7.3 (5H, s), 5.29 (2H, s), 5.0 (1H, bs), 3.85 (2H, d, J=3.3 Hz), 2.21 (1H, m). MS (ES+) C11H11NO2 requires: 189, found: 190 (M+H)+.

Workup

  1. customAfter evaporation of the solvent the resulting residue
  2. customwas purified by flash column chromatography on silica (EtOAc/Petroleum ether 1:10)

Sources & evidence

ORD record
ord-40aeaa6f37fd4664a3dbb9bd18dbfce9
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

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