Reaction #57332

Reaction equation

(S)-(−)-1-(1-naphthyl)ethylamine

K2CO3

methyl 2,3-dibromopropionate

→

title compound

Yield 78.3%

1-(1-Naphthalen-1-yl-ethyl)-aziridine-2-carboxylic acid methyl ester

Yield 78.3%

Solvents

acetonitrile

Conditions

Workup

1. 1
   OtherThe solution is evaporated to dryness
2. 2
   workup.ADDITIONH2O/EtOAc (1:1) (600 mL) is added
3. 3
   Extractionthe mixture is extracted with EtOAc (4×100 mL)
4. 4
   Otherdried
5. 5
   Concentrationconcentrated under vacuum
6. 6
   OtherThe residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:2)

Procedure

To a solution of (S)-(−)-1-(1-naphthyl)ethylamine (20.8 g, 120 mmol) in acetonitrile (HPLC grade, 600 mL) is added K2CO3 (52.7 g, 360 mmol) and methyl 2,3-dibromopropionate (30 g, 120 mmol). The solution is stirred overnight at room temperature. The solution is evaporated to dryness, then H2O/EtOAc (1:1) (600 mL) is added, and the mixture is extracted with EtOAc (4×100 mL). The organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; Hexane/EtOAc 1:2) to provide 24 g (78%) of the title compound as a mixture of two diastereomers in an equimolecular ratio. M+H+=256.10.

Source