反応 #92518

反応方程式

L-alanine methyl ester hydrochloride

1-Naphthalene boronic acid

→

title compound

収率 34.1%

(S)-methyl 2-(naphthalen-1-ylamino)propanoate

収率 34.1%

反応条件

後処理

1. 1
   その他To a dry round bottom flask equipped with a stir bar
2. 2
   その他The flask was sealed with septum
3. 3
   その他evacuated
4. 4
   workup.ADDITIONback filled with O2 atmosphere
5. 5
   workup.ADDITIONTriethyl amine (0.92 mL), and dry DCM (30 mL) were added at room temperature
6. 6
   その他The reaction mixture was quenched with 13 mL 2M NH3 in methanol
7. 7
   その他The volatiles were removed in vacuo
8. 8
   その他the resulting crude oil was purified by silica gel flash chromatography ethyl acetate/n-hexane (10:90)

実験手順

To a dry round bottom flask equipped with a stir bar was added L-alanine methyl ester hydrochloride (500 mg, 3.58 mmol), 1-Naphthalene boronic acid (1000 mg, 5.81 mmol), dry Cu(OAc)2 (715 mg, 3.93 mmol), 4 A° molecular sieves (1.34 g). The flask was sealed with septum, evacuated and back filled with O2 atmosphere. Triethyl amine (0.92 mL), and dry DCM (30 mL) were added at room temperature, stirred for 48 h. The reaction mixture was quenched with 13 mL 2M NH3 in methanol. The volatiles were removed in vacuo and the resulting crude oil was purified by silica gel flash chromatography ethyl acetate/n-hexane (10:90) to give 280 mg of the title compound as brown viscous oil (34% yield).

出典