Triphenylphosphine → 1-[2-[(5-Bromo-3-pyridinyl)oxy]ethyl]-2-pyrrolidinone

HRID 2077567Notes

Reaction equation

HRID 2077567 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][CH2:33][CH2:34][N:35]1[CH2:39][CH2:38][CH2:37][C:36]1=[O:40].[Br:41][C:42]1[CH:43]=[C:44](O)[CH:45]=[N:46][CH:47]=1>C1COCC1>[Br:41][C:42]1[CH:43]=[C:44]([O:32][CH2:33][CH2:34][N:35]2[CH2:39][CH2:38][CH2:37][C:36]2=[O:40])[CH:45]=[N:46][CH:47]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 769801-(2-Hydroxyethyl)-2-pyrrolidinoneHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5995293-Bromo-5-hydroxypyridine

Product 1

HCID 670970361-[2-[(5-Bromo-3-pyridinyl)oxy]ethyl]-2-pyrrolidinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (3 g, 12 mmol) in THF (20 mL) at 0° C. was added the following reagents in order in 10 minutes interval: diethyl azodicarboxylate (2 ml, 12 mmol), 1-(2-hydroxyethyl)pyrrolidin-2-one (0.9 ml, 8 mmol), and 5-bromopyridin-3-ol (2 g, 12 mmol). After 20 min, ice bath was removed; the reaction mixture was warmed up to rt and stirred for 20 h. The reaction was stopped, and solvent was removed The crude product was purified using SiO2 chromatography with hexanes:acetone (70%:30%) solvent system to afford the product as white solid. Wt: 900 mg. MS (ESI pos. ion) m/z: 286.3. Calc'd exact mass for C11H13BrN2O2: 285.14. 1H NMR (300 MHz, chloroform-d) δ ppm 2.04 (none, 1H) 2.41 (d, J=16.37 Hz, 2H) 3.51-3.62 (m, 2H) 3.71 (t, J=5.19 Hz, 2H) 4.16 (t, J=5.19 Hz, 2H) 7.37 (d, J=1.90 Hz, 1H) 8.23 (s, 1H) 8.31 (s, 1H).

Workup

  1. customice bath was removed
  2. customsolvent was removed The crude product
  3. customwas purified

Sources & evidence

ORD record
ord-f119f78ed4a946318bdb6bec7997f07e
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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