1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Azidomethyl-3'-benzyloxybiphenyl

HRID 278169Notes

Reaction equation

HRID 278169 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21]O)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P([N:37]=[N+:38]=[N-:39])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[N:37]([CH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=1)=[N+:38]=[N-:39]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 22627088(3'-Benzyloxybiphenyl-2-yl)methanol

Product 1

HCID 226270842-Azidomethyl-3'-benzyloxybiphenyl

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred solution of (3′-benzyloxybiphenyl-2yl)methanol from Step E (0.994 g, 3.42 mmol) and diphenylphosphoryl azide (1.13 g, 4.10 mmol) in dry toluene (6 mL) at 0° C., under argon, was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.62 g, 4.10 mmol) dropwise. The resulting mixture was stirred and allowed to warm to ambient temperature overnight. Toluene (6 mL) was added and the mixture was washed with water (2×5 mL), then 1.0 N aq. HCl (5 mL), then dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with 5% EtOAc in hexane, to give the titled product as a colorless oil.

Workup

  1. washthe mixture was washed with water (2×5 mL)
  2. dry with material1.0 N aq. HCl (5 mL), then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography
  6. washeluting with 5% EtOAc in hexane

Sources & evidence

ORD record
ord-96a9f7ab33934c62bdeaef89670ea780
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Reaction notes

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