Triphenylphosphine → [4-(1-Azido-ethyl)-3-chloro-phenyl]-carbamic Acid 2-trimethylsilanyl-ethyl Ester

HRID 1385151Notes

Reaction equation

HRID 1385151 reaction equation
[CH3:1][Si:2]([CH3:20])([CH3:19])[CH2:3][CH2:4][O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14](O)[CH3:15])=[C:10]([Cl:17])[CH:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:40]=[N+:41]=[N-:42].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.ClCCl>[CH3:1][Si:2]([CH3:20])([CH3:19])[CH2:3][CH2:4][O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([N:40]=[N+:41]=[N-:42])[CH3:15])=[C:10]([Cl:17])[CH:9]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 24530Hydrazoic acidHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54096646[3-Chloro-4-(1-hydroxy-ethyl)-phenyl]carbamic acid 2-trimethylsilanyl-ethyl ester

Product 1

HCID 53654520[4-(1-Azido-ethyl)-3-chloro-phenyl]-carbamic Acid 2-trimethylsilanyl-ethyl Ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-chloro-4-(1-hydroxy-ethyl)-phenyl]-carbamic acid 2-trimethylsilanyl-ethyl ester (1.25 g) in tetrahydrofuran (20 mL) at 0° C. under an atmosphere of argon is added triphenyl-phosphine (2.6 g), hydrazoic acid (approximately 2.5 molar equivalents in dichloromethane, prepared by the method of Fieser and Fieser, Reagents for Organic Synthesis, Vol. 1, pg. 446: Wiley, N.Y.) and diethyl azodicarboxylate (1.72 g). After approximately 10 minutes the solvent is removed under reduced pressure and the residue is chromatographed over silica gel (5% ethyl acetate in hexanes is used as the eluant) to provide the desired product as a colorless oil.

Workup

  1. customprepared by the method of Fieser and Fieser, Reagents for Organic Synthesis, Vol. 1, pg
  2. customAfter approximately 10 minutes the solvent is removed under reduced pressure
  3. customthe residue is chromatographed over silica gel (5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6ab3899664fc40ab9f27ced967356a1c
Source dataset
uspto-grants-2001_07
Patent number
US06262082B1

Reaction notes

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