Benzyl 4-Hydroxybenzoate → 952589-12-7

HRID 555387Notes

Reaction equation

HRID 555387 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O:40][C:41](=[O:49])[C:42]1[CH:47]=[CH:46][C:45](O)=[CH:44][CH:43]=1)C1C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:45]2[CH:46]=[CH:47][C:42]([C:41]([OH:49])=[O:40])=[CH:43][CH:44]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7180Benzyl 4-HydroxybenzoateHCID 11776TriphenylphosphineHCID 44169391-Boc-3-pyrrolidinolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 22709807952589-12-7Yield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-hydroxy-pyrrolidine-1-carboxylic acid t-butyl ester (3 g, 16.02 mmol) in dry THF (75 mL) was added triphenyl phosphine (4.62 g, 17.62 mmol) and 4-hydroxy-benzoic acid benzyl ester (4.02 g, 17.62 mmol). The reaction mixture was cooled to 0° C. and DEAD (2.78 mL, 17.62 mmol) was added dropwise over a period of 30 min. The reaction was gradually brought to room temperature and stirring continued for 16 hrs. The solvent was removed under vacuum and the residue purified by column chromatography (Flash 40) using a gradient of starting from EtOAc-heptane 1:20 to 1:5. Desired fractions were collected and the solvent evaporated in vacuo. The residue was dissolved in EtOH (80 mL) and 10% Pd/C (0.5 g) was added and the mixture was hydrogenated for 16 hrs. The mixture was filtered and the volatiles were evaporated in vacuo affording 3.4 g (69%) of 3-(4-carboxy-phenoxy)-pyrrolidine-1-carboxylic acid t-butyl ester as a solid.

Workup

  1. customwas gradually brought to room temperature
  2. customThe solvent was removed under vacuum
  3. customthe residue purified by column chromatography (Flash 40)
  4. customDesired fractions were collected
  5. customthe solvent evaporated in vacuo
  6. dissolutionThe residue was dissolved in EtOH (80 mL)
  7. addition10% Pd/C (0.5 g) was added
  8. waitthe mixture was hydrogenated for 16 hrs
  9. filtrationThe mixture was filtered
  10. customthe volatiles were evaporated in vacuo

Sources & evidence

ORD record
ord-dee2548d347f4a3abf9490eb41fb0846
Source dataset
uspto-grants-2011_11
Patent number
US08053447B2

Reaction notes

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