Triphenylphosphine → HCID 59599448, compound

HRID 2266711Notes

Reaction equation

HRID 2266711 reaction equation
CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:32][C:33]1[CH:34]=[N:35][NH:36][CH:37]=1.[C:38]([O:42][C:43](=[O:49])[N:44]([CH2:46][CH2:47]O)[CH3:45])([CH3:41])([CH3:40])[CH3:39]>C1COCC1>[C:38]([O:42][C:43](=[O:49])[N:44]([CH2:46][CH2:47][N:35]1[CH:34]=[C:33]([Br:32])[CH:37]=[N:36]1)[CH3:45])([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 163754-BromopyrazoleHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 59599448HCID 59599448, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethylazodicarboxylate (0.48 mL, 3.1 mmol) was added to a 0° C. solution of triphenylphosphine (0.80 g, 3.1 mmol) in THF (20 mL). After stirring for 5 minutes, 4-bromopyrazole (0.30 mg, 2.0 mmol) was added. After another 5 minutes of stirring, (2-hydroxyethyl)-methyl-carbamic acid tert-butyl ester (0.45 g, 2.6 mmol) was added. The reaction was allowed to warm to room temperature and stir overnight. The reaction was cooled to 0° C. and filtered. The filtrate was concentrated by rotary evaporation. The residue was purified by silica gel chromatography using gradient elution of dichloromethane, ethyl acetate to afford [2-(4-bromo-pyrazol-1-yl)-ethyl]-methyl-carbamic acid tert-butyl ester (541 mg, 87%).

Workup

  1. stirringAfter another 5 minutes of stirring
  2. stirringstir overnight
  3. temperatureThe reaction was cooled to 0° C.
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated by rotary evaporation
  6. customThe residue was purified by silica gel chromatography
  7. washelution of dichloromethane, ethyl acetate

Sources & evidence

ORD record
ord-ffb1e9dd1d104af3bf1dc9b01580445d
Source dataset
uspto-grants-2010_12
Patent number
US07858643B2

Reaction notes

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