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

HRID 844303Notes

Reaction equation

HRID 844303 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-8c0a0952689a43859c3607455de40169
Source dataset
uspto-grants-2002_04
Patent number
US06380243B1

Reaction notes

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