Triphenylphosphine → HCID 66653163, compound

HRID 1524281Notes

Reaction equation

HRID 1524281 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.O[C@@H:13]1[CH2:17][CH2:16][NH:15][C:14]1=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C@@H:13]2[CH2:17][CH2:16][NH:15][C:14]2=[O:18])[CH:5]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 88068Methyl 3-HydroxybenzoateHCID 641547(R)-3-Hydroxypyrrolidin-2-oneHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 66653163HCID 66653163, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cool a solution of 3-hydroxy-benzoic acid methyl ester (9.03 g, 59.4 mmol) in tetrahydrofuran (125 mL) to 0° C. and add (R)-3-hydroxy-pyrrolidin-2-one (5.00 g, 49.5 mmol) and triphenyl phosphine (15.6 g, 59.4 mmol). Slowly add to this mixture diethylazodicarboxylate (10.2 mL, 64.3 mmol). Warm the reaction mixture to room temperature and stir overnight. Concentrate the mixture under reduced pressure and purify the residue by flash silica gel chromatography to provide 11.2 g of 3-((R)-2-oxo-pyrrolidin-3-yloxy)-benzoic acid methyl ester as an oil.

Workup

  1. concentrationConcentrate the mixture under reduced pressure
  2. custompurify the residue by flash silica gel chromatography

Sources & evidence

ORD record
ord-10ba48ca085c4fd387980efbdafe65af
Source dataset
uspto-grants-2015_07
Patent number
US09079880B2

Reaction notes

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