Triphenylphosphine → (R)-4-((R)-1-(7-(pyridin-2-yl)quinolin-5-yloxy)ethyl)pyrrolidin-2-one

HRID 1402713Notes

Reaction equation

HRID 1402713 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[C:9]([OH:17])[C:10]2[CH:11]=[CH:12][CH:13]=[N:14][C:15]=2[CH:16]=1.O[C@H:19]([C@H:21]1[CH2:25][N:24]([C@H](C2C=CC(OC)=CC=2)C)[C:23](=[O:36])[CH2:22]1)[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[N:14]2)=[C:9]([O:17][C@@H:19]([C@H:21]2[CH2:25][NH:24][C:23](=[O:36])[CH2:22]2)[CH3:20])[CH:8]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 58071870(R)-4-((S)-1-hydroxyethyl)-1-((S)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-oneHCID 1364132527-(Pyridin-2-yl)quinolin-5-ol

Product 1

HCID 71238245(R)-4-((R)-1-(7-(pyridin-2-yl)quinolin-5-yloxy)ethyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

20 mg of 7-(Pyridin-2-yl)quinolin-5-ol, 30 mg of ((R)-4-((S)-1-hydroxyethyl)-1-((S)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one and 50 mg of triphenylphosphin was dissolved in 2 mL of DCM. 45 mg of DBAD was added and the mixture stirred for 14 h at room temperature. The mixture was diluted with DCM and extracted with 1N NaOH and water. The organic phase was concentrated in vacuo and dissolved in 0.5 mL of TFA and heated 30 min at 90° C. in the microwave. The mixture was purified with HPLC (XbridgeC18, MeOH/water, TFA) to yield after lyophilisation 21 mg of Example 6 as solid.

Workup

  1. extractionextracted with 1N NaOH and water
  2. concentrationThe organic phase was concentrated in vacuo
  3. dissolutiondissolved in 0.5 mL of TFA
  4. temperatureheated 30 min at 90° C. in the microwave
  5. customThe mixture was purified with HPLC (XbridgeC18, MeOH/water, TFA)

Sources & evidence

ORD record
ord-fe28971e8b7e4d9abc1a3b589818a4cb
Source dataset
uspto-grants-2014_12
Patent number
US08912173B2

Reaction notes

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