Triphenylphosphine → HCID 67027251, compound

HRID 2400330Notes

Reaction equation

HRID 2400330 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]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[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:26]2[CH2:27][CH2:22][CH2:23][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:25]2)[CH:20]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 163754-BromopyrazoleHCID 5456991-Boc-3-hydroxypiperidineHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 67027251HCID 67027251, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIAD (1.18 ml, 6.0 ml) was added dropwise to a solution of 4-bromopyrazole (0.74 g, 5.0 mmol), 3-hydroxy-1-tert-butoxycarbonylpiperidine (1.00 g, 5.0 mmol) and triphenylphosphine (1.57 g, 6.0 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. The organic fractions were washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (50% EtOAc/Petrol) to give the product (1.46 g). MS: [M+H]+=332.

Workup

  1. customThe reaction was partitioned between water and ethyl acetate
  2. washThe organic fractions were washed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (50% EtOAc/Petrol)

Sources & evidence

ORD record
ord-590f735b0ffb49c2bcdc00d6e3c22b6e
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

Loading…