1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86619586, compound

HRID 2236684Notes

Reaction equation

HRID 2236684 reaction equation
[CH2:1]([O:8][C:9]1[C:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C:13]=2[CH:12]=[C:11]([CH2:20]O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P([N:36]=[N+:37]=[N-:38])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>O1CCCC1>[N:36]([CH2:20][C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C:13]=2[CH:12]=1)=[N+:37]=[N-:38]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 68697080HCID 68697080, compound

Product 1

HCID 86619586HCID 86619586, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. mixture of (7-benzyloxy-2,2-dimethyl-benzo[1,3]dioxol-5-yl)-methanol (0.57 g, 2.0 mmol) and diphenylphosphoryl azide (0.52 mL, 2.4 mmol) in tetrahydrofuran (10 mL) is added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 0.33 mL, 2.2 mmol). The mixture is allowed to warm to room temperature over the weekend and then quenched with the addition of water. The reaction mixture is extracted 3× with ethyl acetate, and the combined extracts were washed with 5% aqueous potassium hydrogen sulfate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated to give 6-azidomethyl-4-benzyloxy-2,2-dimethyl-benzo[1,3]dioxole, which is used in the next step without purification.

Workup

  1. customquenched with the addition of water
  2. extractionThe reaction mixture is extracted 3× with ethyl acetate
  3. washthe combined extracts were washed with 5% aqueous potassium hydrogen sulfate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-10eb2d064bdf459ca285b3e35091340a
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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