(3S)-3-hydroxypyrrolidin-2-one → (R)-3-((6-ethoxypyridin-3-yl)oxy)pyrrolidin-2-one

HRID 533919Notes

Reaction equation

HRID 533919 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][NH:4][C:3]1=[O:7].[CH2:8]([O:10][C:11]1[N:16]=[CH:15][C:14](O)=[CH:13][CH:12]=1)[CH3:9]>C1COCC1>[CH2:8]([O:10][C:11]1[N:16]=[CH:15][C:14]([O:1][C@@H:2]2[CH2:6][CH2:5][NH:4][C:3]2=[O:7])=[CH:13][CH:12]=1)[CH3:9]

Participants

4

Reactant 2

HCID 11029774(3S)-3-hydroxypyrrolidin-2-oneHCID 140678626-Ethoxypyridin-3-ol

Product 1

HCID 86715109(R)-3-((6-ethoxypyridin-3-yl)oxy)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-3-hydroxy-pyrrolidin-2-one (8.07 g), 6-ethoxypyridin-3-ol (11.0 g) and THF (100 mL) was purged with argon. Triphenylphosphine (20.7 g) was added followed by slow addition of DIAD (16.0 g). After 2 hours the mixture was concentrated and the residue purified by SGC (eluent: EA) to provide the subtitle compound. MS ESI+: m/z=223 [M+H]+.

Workup

  1. customwas purged with argon
  2. additionTriphenylphosphine (20.7 g) was added
  3. additionfollowed by slow addition of DIAD (16.0 g)
  4. concentrationAfter 2 hours the mixture was concentrated
  5. customthe residue purified by SGC (eluent: EA)

Sources & evidence

ORD record
ord-3a67f1e989e24a9f844e4d96d78555b3
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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