Ethanol → (4-Hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 12923

Reaction equation

HRID 12923 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH: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].CCO>C1COCC1.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH: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 702EthanolHCID 597530242-(4-Benzyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59752861(4-Hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from step 1, in THF (11 ml), EtOH (25 ml), Pd—C (1.17 g, 10% wt) in a round bottom flask was charged with H2-balloon after flushing with hydrogen 3 times. The resulting solution was stirred overnight at rt. The reaction mixture was then filtered, washed with THF (30 ml), EtOH (25 ml) and dried over anhydrous MgSO4. After removal of the solvent in vacuo, the product was obtained as an orange oil (1.0 g, 95%).

Workup

  1. customafter flushing with hydrogen 3 times
  2. filtrationThe reaction mixture was then filtered
  3. washwashed with THF (30 ml), EtOH (25 ml)
  4. dry with materialdried over anhydrous MgSO4
  5. customAfter removal of the solvent in vacuo

Sources & evidence

ORD record
ord-c572fd6f9a4547b19a9a8a4f102b77ad
Source dataset
uspto-grants-2010_06
Patent number
US07728032B2

Linked notes

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