Triphenylphosphine → HCID 67027580, compound

HRID 2400329Notes

Reaction equation

HRID 2400329 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Br:15][C:16]1[CH:17]=[N:18][NH:19][CH:20]=1.O[CH:22]1[CH2:27][CH2:26][CH2:25][N:24]([CH3:28])[CH2:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:15][C:16]1[CH:17]=[N:18][N:19]([CH:22]2[CH2:27][CH2:26][CH2:25][N:24]([CH3:28])[CH2:23]2)[CH:20]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 163754-BromopyrazoleHCID 980163-Piperidinol, 1-methyl-HCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 67027580HCID 67027580, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIAD (3.21 ml, 16.3 ml) was added dropwise to a solution of 4-bromopyrazole (2.0 g, 13.6 mmol), 3-hydroxy-1-methylpiperidine (1.57 ml, 13.6 ml) and triphenylphosphine (4.3 g, 16.3 mmol) in THF (50 ml) at 0° C. The mixture was allowed to warm to room temperature and stirred overnight. The reaction was partitioned between water and ethyl acetate and the organic layers were extracted into 2N HCl. The aqueous fraction was basified with sodium bicarbonate and extracted into ethyl acetate. The organic fractions were dried (MgSO4), filtered and concentrated under reduced pressure to give the product (1.64 g), which was used without purification. MS: [M+H]+=244.

Workup

  1. customThe reaction was partitioned between water and ethyl acetate
  2. extractionthe organic layers were extracted into 2N HCl
  3. extractionextracted into ethyl acetate
  4. dry with materialThe organic fractions were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4f3734f0a6b5475b8a72e54de247c395
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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