Water → HCID 71548967, compound

HRID 590547Notes

Reaction equation

HRID 590547 reaction equation
[N:1]([CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][Si:20]([CH3:24])([CH3:23])[CH2:19][CH2:18]3)=[C:13]([F:25])[CH:12]=2)[CH2:6]1)=[N+:2]=[N-:3].O.O1CCO[CH2:29][CH2:28]1>>[N:1]1([CH2:4][C@@H:5]2[O:9][C:8](=[O:10])[N:7]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22][CH2:21][Si:20]([CH3:23])([CH3:24])[CH2:19][CH2:18]4)=[C:13]([F:25])[CH:12]=3)[CH2:6]2)[CH:29]=[CH:28][N:3]=[N:2]1

Participants

4

Reactant 3

HCID 962WaterHCID 312751,4-DioxaneHCID 71548966HCID 71548966, compound

Product 1

HCID 71548967HCID 71548967, compound

Procedure

A solution of azide 19 (0.60 mmol) and bicyclodiene 20 (0.31 mL, 3.03 mmol) in dioxane (4.0 mL) is refluxed for 5 h. Water (5 mL) is added and extracted with DCM (2×5 mL), dried and concentrated. The product is further purified by column chromatography on silica using hexane-EtOAc mixtures to obtain the product as a brown solid (60 mg) in 26% over 3 steps.

Workup

  1. extractionextracted with DCM (2×5 mL)
  2. customdried
  3. concentrationconcentrated
  4. customThe product is further purified by column chromatography on silica

Sources & evidence

ORD record
ord-c3077d976dc34ff8b9d9e310dfeb5162
Source dataset
uspto-grants-2016_01
Patent number
US09233989B2

Reaction notes

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