Tert-Butylamine → HCID 66617859, compound

HRID 532797Notes

Reaction equation

HRID 532797 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.C1COCC1.[C:19]([NH2:23])([CH3:22])([CH3:21])[CH3:20]>C(O)C>[C:19]([NH:23][CH2:13][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:9]([O:11][CH3:12])=[O:10])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 8028TetrahydrofuranHCID 11735736Methyl 2-(4-chlorophenyl)acrylate

Product 1

HCID 66617859HCID 66617859, compoundYield 422.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of methyl 2-(4-chlorophenyl)acrylate (2.00 g, 10.2 mmol) in 1:1 THF:ethanol (20 mL) was treated with tert-butyl amine (389 uL, 2.23 mmol) at 60° C. The reaction stirred for 20 hours to completion, and the solvent/excess amine were removed in vacuo. The residue was purified by chromatography on silica gel (eluted with 1:1 hexanes:ethyl acetate) to afford the pure methyl 3-(tert-butylamino)-2-(4-chlorophenyl)propanoate (2.54 g, 93%) as a colorless oil. LCMS (APCI+) m/z 270.0 [M+H]+.

Workup

  1. customthe solvent/excess amine were removed in vacuo
  2. customThe residue was purified by chromatography on silica gel (eluted with 1:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-8a75b2dc38134ade8012fb06c779125d
Source dataset
uspto-grants-2014_10
Patent number
US08853199B2

Reaction notes

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