Azidotrimethylsilane → HCID 25241962, compound

HRID 708331Notes

Reaction equation

HRID 708331 reaction equation
[C:1]([NH:8][CH2:9][C:10]#[CH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C[Si]([N:16]=[N+:17]=[N-:18])(C)C>CN(C=O)C.CO.[Cu]I>[N:16]1[NH:17][N:18]=[C:10]([CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH:11]=1

Participants

5

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamate

Product 1

HCID 25241962HCID 25241962, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 21901440N,N-dimethylformamide methanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-Boc-propargyl amine (1.60 g, 10.3 mmol) in a mixture of DMF:MeOH (4:1, 10 mL) was added trimethylsilylazide (2.0 mL, 15.2 mmol) and CuI (95 mg, 0.50 mmol). The resulting mixture was heated to 100° C. for 16 h, whereupon it was concentrated in vacuo and purified via silica gel chromatography, affording the title compound (2.0 g, 99%) as a light yellow oil; LCMS: m/z=196.9 (M−1).

Workup

  1. concentrationwas concentrated in vacuo
  2. custompurified via silica gel chromatography

Sources & evidence

ORD record
ord-717d23fe639a4643b9a6aadf72a27996
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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