Triphenylphosphine Oxide → HCID 86655327, compound

HRID 877002Notes

Reaction equation

HRID 877002 reaction equation
Br[CH2:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])[CH:6]=[CH:5][CH:4]=1.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N-:35]=[N+:36]=[N-:37].[Na+]>CN(C=O)C>[N:35]([CH2:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])[CH:6]=[CH:5][CH:4]=1)=[N+:36]=[N-:37]

Participants

5

Reactant 3

HCID 13097Triphenylphosphine OxideHCID 33557Sodium AzideHCID 66718402HCID 66718402, compound

Product 1

HCID 86655327HCID 86655327, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(6-bromomethylpyridin-2-yl)pyrrolidin-2-one (10.19 g, 39.94 mop containing triphenylphosphine oxide impurity in DMF (80 mL) was treated with sodium azide (2.60 g, 39.94 mmol), stirred for 18 h and partitioned between EtOAc and water. The organic phase was separated and the aqueous phase re-extracted with EtOAc (×2). The combined organic extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow oil, contaminated with triphenylphosphine oxide; used in the next step without further purification; LC-MS retention time 2.19 min, (M+H)+ 218.

Workup

  1. custompartitioned between EtOAc and water
  2. customThe organic phase was separated
  3. extractionthe aqueous phase re-extracted with EtOAc (×2)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22fe9efd6e36464cab44084aee96fa6a
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

Loading…