tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate → Tyramine

HRID 1746254Notes

Reaction equation

HRID 1746254 reaction equation
C([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)(OC(C)(C)C)=O.Cl.O1CCOCC1>C(OCC)(=O)C>[NH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 5610TyramineYield 160.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl acetate (1.5 mL) was added to 100 mg of Boc-Tyramine-PEM (α,γ-mixture) obtained in Reference Example 3 to suspend the compound, and then 4 N HCl/dioxane (0.5 mL) was added thereto. The mixture was stirred for one hour at room temperature. A precipitate thus obtained was filtered with a Kiriyama funnel and dried in a vacuum, and thus 93 mg of Tyramine-PEM (α,γ-mixture) was obtained. The compound is thought to be a dihydrochloride salt, based on yield.

Workup

  1. customobtained in Reference Example 3
  2. customA precipitate thus obtained
  3. filtrationwas filtered with a Kiriyama funnel
  4. customdried in a vacuum

Sources & evidence

ORD record
ord-fd045853c3d74b72a0979ba819f46f1f
Source dataset
uspto-grants-2015_10
Patent number
US09149540B2

Reaction notes

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