[4-(4-Benzyloxycarbonylaminobutyl)phenoxy]acetic acid ethyl ester → Ethyl [4-(4-aminobutyl)phenoxy]acetate

HRID 1678301Notes

Reaction equation

HRID 1678301 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17]C(OCC2C=CC=CC=2)=O)=[CH:9][CH:8]=1)[CH3:2].[H][H]>[Pd].CO>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 2

HCID 21031128[4-(4-Benzyloxycarbonylaminobutyl)phenoxy]acetic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 67351631Ethyl [4-(4-aminobutyl)phenoxy]acetateYield 88.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 42 (1.11 g, 2.88 mmol) and 10% palladium on carbon (0.40 g, wet) in methanol (50 mL) was stirred at room temperature for 2 h under atmospheric pressure of hydrogen. The mixture was then filtered through a silica gel pad. The solvent was evaporated to provide 43 (0.64 g, 88%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.21 (m, 3H), 1.30-1.63 (m, 6H), 3.13 (m, 2H), 4.17 (m, 2H), 4.72 (br s, 2H), 6.84 (m, 2H), 7.10 (m, 2H).

Workup

  1. filtrationThe mixture was then filtered through a silica gel pad
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9bd8fb42e5cf40828c0f6336b3961a0b
Source dataset
uspto-grants-2011_08
Patent number
US08008494B2

Reaction notes

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