Triphenylphosphine → HCID 68162340, compound

HRID 2041698Notes

Reaction equation

HRID 2041698 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.N(/C(OC(C)C)=O)=N\C(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:49][CH2:50][N:51]([CH3:59])[C:52](=[O:58])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55]>C1COCC1>[CH3:59][N:51]([CH2:50][CH2:49][N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)[CH:10]=[N:11]1)[C:52](=[O:58])[O:53][C:54]([CH3:55])([CH3:57])[CH3:56]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 68162340HCID 68162340, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (5 g, 25.8 mmol), bis(1-methylethyl) (E)-1,2-diazenedicarboxylate (5.73 g, 28.3 mmol), triphenylphosphine (7.43 g, 28.3 mmol) and 1,1-dimethylethyl (2-hydroxyethyl)methylcarbamate (4.52 g, 25.8 mmol) were dissolved in THF at 0° C. under nitrogen and the resulting mixture was stirred at this temperature for 4 h, then evaporated in vacuo and the residue triturated with MTBE. The precipitated solid was removed by filtration and the filtrate evaporated in vacuo, then purified by chromatography on silica gel (gradient:0-100% EtOAc in Hexanes) to give 1,1-dimethylethyl methyl{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]ethyl}carbamate (4.85 g, 13.81 mmol, 53.6% yield) as a colourless oil.

Workup

  1. customevaporated in vacuo
  2. customthe residue triturated with MTBE
  3. customThe precipitated solid was removed by filtration
  4. customthe filtrate evaporated in vacuo
  5. custompurified by chromatography on silica gel (gradient:0-100% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-49cbd29965ff44b896a43173d7ebd012
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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