2-(3-t-Butyl-4-hydroxyphenyl)-1-(1,3,4-oxadiazol-2-yl)ethylcarbamic acid benzyl ester → 2-(3-t-Butyl-4-hydroxyphenyl)-1-(1,3,4-oxadiazol-2-yl)ethylamine

HRID 1988267Notes

Reaction equation

HRID 1988267 reaction equation
C(OC(=O)[NH:10][CH:11]([C:24]1[O:25][CH:26]=[N:27][N:28]=1)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:14]=1)C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[C:20]([C:15]1[CH:14]=[C:13]([CH2:12][CH:11]([NH2:10])[C:24]2[O:25][CH:26]=[N:27][N:28]=2)[CH:18]=[CH:17][C:16]=1[OH:19])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 2

HCID 867609002-(3-t-Butyl-4-hydroxyphenyl)-1-(1,3,4-oxadiazol-2-yl)ethylcarbamic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 178192112-(3-t-Butyl-4-hydroxyphenyl)-1-(1,3,4-oxadiazol-2-yl)ethylamineYield 97%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(3-t-butyl-4-hydroxyphenyl)-1-(1,3,4-oxadiazol-2-yl)ethylcarbamic acid benzyl ester (1.25 g, 3.16 mmol) in methanol (30 ml), 10% palladium carbon (130 mg) was added and stirred in a hydrogen atmosphere at room temperature for 1 day. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: chloroform:methanol:aqueous ammonia=100:10:1), giving the titled compound (0.80 g, 97%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9b220cad92d14557a09cd4eac5ff3a19
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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