Triphenylphosphine → (R)-3-((6-(cyclopropylmethoxy)pyridin-3-yl)oxy)pyrrolidin-2-one

HRID 533900Notes

Reaction equation

HRID 533900 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][C:3]1=[O:7].[CH2:8]1[CH2:10][CH:9]1[CH2:11][O:12][C:13]1[N:18]=[CH:17][C:16](O)=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.C(Cl)Cl>[CH2:8]1[CH2:10][CH:9]1[CH2:11][O:12][C:13]1[N:18]=[CH:17][C:16]([O:1][C@@H:2]2[CH2:6][CH2:5][NH:4][C:3]2=[O:7])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11029774(3S)-3-hydroxypyrrolidin-2-oneHCID 575175006-(Cyclopropylmethoxy)pyridin-3-ol

Product 1

HCID 86715086(R)-3-((6-(cyclopropylmethoxy)pyridin-3-yl)oxy)pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-3-hydroxy-pyrrolidin-2-one (3.00 g), 6-(2-cyclopropyl-methoxy)-pyridin-3-ol (4.90 g), triphenylphosphine (polymer, 8.56 g), DCM (30 mL) and THF (50 mL) was added DIAD (6.60 g) keeping the reaction temperature below 30° C. After 12 hours the mixture was filtered and the filtrate was evaporated. The residue was purified by SGC (eluent: EA/MeOH 9:1) to provide the title compound. MS ESI+: m/z=249 [M+H]+.

Workup

  1. customthe reaction temperature below 30° C
  2. filtrationAfter 12 hours the mixture was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was purified by SGC (eluent: EA/MeOH 9:1)

Sources & evidence

ORD record
ord-b484d0adc3404aff9cc1dd19ad6ffaaa
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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