4-Chlorophenol → HCID 59166750, compound

HRID 1442962Notes

Reaction equation

HRID 1442962 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].[Cl:18][C:19]1[CH:24]=[CH:23][C:22](O)=[CH:21][CH:20]=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>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([O:10][C:22]2[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=2)[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 11776TriphenylphosphineHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 59166750HCID 59166750, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2S,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (CAS Reg. No. 74844-91-0) (1.10 g, 4.08 mmol) was dissolved in THF (25 ml) and 4-chlorophenol (0.78 g, 6.12 mmol) and triphenylphosphine (1.6 g, 6.12 mmol) were added. The solution was cooled in and ice bath and DIAD (0.96 ml, 4.88 mmol) added dropwise. The reaction was stirred at room temperature overnight. After evaporation of the solvent, the residue was dissolved in diethylether (20 ml) and pentane added until solution was only just maintained. The solution was seeded with triphenylphosphine oxide and cooled in ice. The resultant precipitate was filtered and the filtrate evaporated. The residue was purified by flash chromatography on silica (100 g), loading with pentane:diethylether (2:1 by volume) and eluting with pentane : diethylether (1: 1 by volume) to give the title compound as a colourless oil (1.35 g, 69%) containing a small impurity of diisopropylbicarbamate (CAS Reg. No.19740-72-8) by NMR.

Workup

  1. temperatureThe solution was cooled in and ice bath
  2. customAfter evaporation of the solvent
  3. dissolutionthe residue was dissolved in diethylether (20 ml)
  4. additionpentane added until solution
  5. temperaturewas only just maintained
  6. temperaturecooled in ice
  7. filtrationThe resultant precipitate was filtered
  8. customthe filtrate evaporated
  9. customThe residue was purified by flash chromatography on silica (100 g)
  10. washeluting with pentane : diethylether (1: 1 by volume)

Sources & evidence

ORD record
ord-48e3a1580a7348819433c84b30127d99
Source dataset
uspto-grants-2010_02
Patent number
US07659305B2

Reaction notes

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