Phenol → HCID 57315333, compound

HRID 412661Notes

Reaction equation

HRID 412661 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C@H:4]([CH2:17][OH:18])[CH2:3]1.[C:19]1(O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[C@H:4]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 14994791Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 57315333HCID 57315333, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl (2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate (2.0 g) [see Ceulemans et al, Chem. Eur. J. (1997), 3(12), 1997-2010] was added to a solution of phenol (1.12 g), triphenylphosphine (2.51 g) and diethylazodicarboxylate (1.51 ml) in dry tetrahydrofuran (40 ml). The reaction mixture was stirred at room temperature for 20 hours, after which time the solvent was removed under reduced pressure and the residue was dissolved in chloroform. The organic solution was washed with 15% aqueous sodium hydroxide solution, then brine, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent system of 1:1, by volume, hexane:ethyl acetate to afford benzyl (2S,4R)-4-hydroxy-2-(phenoxymethyl)pyrrolidine-1-carboxylate (0.69 g) as a clear oil.

Workup

  1. customafter which time the solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe organic solution was washed with 15% aqueous sodium hydroxide solution
  4. dry with materialbrine, dried over magnesium sulphate
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel eluting with a solvent system of 1:1, by volume, hexane

Sources & evidence

ORD record
ord-1d97fe69eafd402291ed48861abffeec
Source dataset
uspto-grants-2003_05
Patent number
US06562964B1

Reaction notes

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