9-Fluorenylmethyl chloroformate → (9H-fluoren-9-yl)methyl prop-2-yn-1-ylcarbamate

HRID 1371264Notes

Reaction equation

HRID 1371264 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].C(N(C(C)C)CC)(C)C.Cl[C:15]([O:17][CH2:18][CH:19]1[C:31]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16]>CN(C)C=O>[CH:30]1[C:31]2[CH:19]([CH2:18][O:17][C:15](=[O:16])[NH:4][CH2:1][C:2]#[CH:3])[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:26]=2[CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 343679-Fluorenylmethyl chloroformateHCID 81531DiisopropylethylamineHCID 239041Propargylamine

Product 1

HCID 10084877(9H-fluoren-9-yl)methyl prop-2-yn-1-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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).

Workup

  1. extractionAn ethyl acetate/water extraction procedure
  2. customto isolate the product

Sources & evidence

ORD record
ord-1de5453cc2804d7191729f99e8a78bf8
Source dataset
uspto-grants-2007_01
Patent number
US07157434B2

Reaction notes

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