1,8-Diazabicyclo(5.4.0)undec-7-ene → (5-Azidomethyl-furan-2-ylmethyl)-carbamic Acid Tert-Butyl Ester

HRID 34105Notes

Reaction equation

HRID 34105 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[O:10][C:11]([CH2:14]O)=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].N12CCCN=C1CCCCC2.C1(P([N:42]=[N+:43]=[N-:44])(C2C=CC=CC=2)=O)C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[O:10][C:11]([CH2:14][N:42]=[N+:43]=[N-:44])=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 60034672tert-butyl N-{[5-(hydroxymethyl)furan-2-yl]methyl}carbamate

Product 1

HCID 60053847(5-Azidomethyl-furan-2-ylmethyl)-carbamic Acid Tert-Butyl EsterYield 80.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

99.4 mg of (5-hydroxymethyl-furan-2-ylmethyl)-carbamic acid tert-butyl ester was added to 4.5 mL of toluene, added successively with 83.7 mg of 1,8-diazabicyclo[5,4,0]undec-7-ene and 151.6 mg of diphenylphosphoryl azide, and stirred at room temperature under nitrogen atmosphere for 1 hour and 45 minutes. Then the solvent was evaporated, followed by purification and separation by silica gel column chromatography, to afford 88.6 mg of the title compound as a colorless oil.

Workup

  1. customThen the solvent was evaporated
  2. customfollowed by purification and separation by silica gel column chromatography

Sources & evidence

ORD record
ord-c19f5c57d04244d78f3d083d4436c690
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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