Triethylamine → HCID 40493097, compound

HRID 1842707Notes

Reaction equation

HRID 1842707 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[C:7]1([C@H:13]([NH2:15])[CH3:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>CCOC(C)=O>[C:7]1([C@H:13]([NH:15][CH2:2][C:3]([O:5][CH3:6])=[O:4])[CH3:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 40493097HCID 40493097, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

Methyl 2-bromoacetate (621 g, 4.1 mol) was added dropwise to a mixture of (1R)-1-phenylethanamine (410 g, 3.4 mol) and triethylamine (377 g, 3.7 mol) in EtOAc (4.5 L) at r.t. The mixture was then stirred at 50-60° C. overnight then cooled to r.t. The mixture was then washed with water (800 mL) and brine (100 mL), dried (Na2SO4) and concentrated in vacuo to give the title compound (587 g, 90%) as yellow oil; 1H NMR: (CDCl3) 1.29 (3H, d), 3.13-3.24 (2H, m), 3.60 (3H, s), 3.68-3.71 (1H, m), 7.13-7.26 (5H, m).

Workup

  1. temperaturethen cooled to r.t
  2. washThe mixture was then washed with water (800 mL) and brine (100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51a8c7e831a942c7b2d7873ef204d84a
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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