Methyl bromoacetate → HCID 66629732, compound

HRID 882343Notes

Reaction equation

HRID 882343 reaction equation
C(N(CC)C(C)C)(C)C.Cl.[C:11]1([C@@H:17]2[CH2:19][C@H:18]2[NH2:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Br[CH2:22][C:23]([O:25][CH3:26])=[O:24]>CC#N>[C:11]1([C@@H:17]2[CH2:19][C@H:18]2[NH:20][CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 2723716Tranylcypromine hydrochloride

Product 1

HCID 66629732HCID 66629732, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N-Diisopropylethylamine (3 mL, 17.16 mmol) was added to a solution of (trans)-2-phenylcyclopropanamine hydrochloride (1.5 g, 8.58 mmol) in 70 mL of CH3CN. After complete dissolution of the amine the methyl 2-bromoacetate (930 μL, 9.44 mmol) was added and then stirred overnight at room temperature. After solvent removal the crude was purified by flash chromatography eluting with CH2Cl2/MeOH (99:1 to 90:10) to get methyl 2-((trans)-2-phenylcyclopropylamino)acetate as colourless oil (1.76 g, Yield=100%).

Workup

  1. additionwas added
  2. customAfter solvent removal the crude
  3. customwas purified by flash chromatography
  4. washeluting with CH2Cl2/MeOH (99:1 to 90:10)

Sources & evidence

ORD record
ord-5b1f960cc73047778fe22fce717957c3
Source dataset
uspto-grants-2015_03
Patent number
US08993808B2

Reaction notes

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