1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18433602, compound

HRID 2306190Notes

Reaction equation

HRID 2306190 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)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:38]=[N+:39]=[N-:40])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]([N:38]=[N+:39]=[N-:40])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 11782317HCID 11782317, compound

Product 1

HCID 18433602HCID 18433602, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of (3-benzyloxyphenyl)(3-chlorophenyl)methanol, as described above in Step A, (4.0 g, 12.3 mmol) and diphenylphosphoryl azide (4.1 g, 14.9 mmol) in dry toluene (35 mL) at 0° C., was added 1,8-diazabicyclo[5.4.0]undec-7-ene (2.1 g, 13.8 mmol). The resulting mixture was allowed to warm to ambient temperature, and stirred under argon for 18 hours, then washed with 5% hydrochloric acid (10 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with hexane—2% EtOAc to yield the product as a colorless oil.

Workup

  1. washwashed with 5% hydrochloric acid (10 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography on silica
  6. washeluting with hexane—2% EtOAc

Sources & evidence

ORD record
ord-606c5d8027de4cd98435d6de6badc488
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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