Reaction #1458446

ord-1de5453cc2804d7191729f99e8a78bf8

Reaction equation

C#CCN
propargylamine
CCN(C(C)C)C(C)C
diisopropylethylamine
O=C(Cl)OCC1c2ccccc2-c2ccccc21
9-fluorenylmethyl chloroformate
→
C#CCNC(=O)OCC1c2ccccc2-c2ccccc21
Prop-2-ynyl-carbamic acid 9H-fluoren-9-ylmethyl ester

Reactants

C#CCN
propargylamine
CCN(C(C)C)C(C)C
diisopropylethylamine
O=C(Cl)OCC1c2ccccc2-c2ccccc21
9-fluorenylmethyl chloroformate

Reagents

None

Solvents

CN(C)C=O
dimethylformamide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ExtractionAn ethyl acetate/water extraction procedure
  2. 2
    Otherto isolate the product

Procedure

To a solution of propargylamine (250 μL, 3.645 mmol) in diisopropylethylamine (1.273 mL, 7.290 mmol), was added 9-fluorenylmethyl chloroformate (Fmoc), dissolved in 7 mL dimethylformamide. The mixture was stirred under argon overnight at room temperature. After completion, the solution was reduced in vacuo. An ethyl acetate/water extraction procedure was performed to isolate the product; MS: 278.10 (m/z).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07157434B2uspto-grants-2007_01