Tetrahydrofuran → (R)-2-(4-Hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1909811Notes

Reaction equation

HRID 1909811 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21]CC2C=CC=CC=2)=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1>[Pd].CCO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 68999348(R)-2-(4-Benzyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68999591(R)-2-(4-Hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product from step 2 (12.0 g, 31.3 mmol) was added to a round-bottom flask containing THF (100 mL), EtOH (200 mL) and 10% Pd/C (10.5 g). The flask was charged with H2 and left to stir under H2 atmosphere overnight. The Pd/C was removed by filtering the reaction mixture through celite. The resulting solution was concentrated to give the title compound. (6.00 g, 65%).

Workup

  1. additionThe flask was charged with H2
  2. waitleft
  3. customThe Pd/C was removed
  4. filtrationby filtering the reaction mixture through celite
  5. concentrationThe resulting solution was concentrated

Sources & evidence

ORD record
ord-176c43749cd9419692d41dd09d4ea095
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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