Reaction #92518

Reaction equation

L-alanine methyl ester hydrochloride

1-Naphthalene boronic acid

→

title compound

Yield 34.1%

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

Yield 34.1%

Conditions

Workup

1. 1
   OtherTo a dry round bottom flask equipped with a stir bar
2. 2
   OtherThe flask was sealed with septum
3. 3
   Otherevacuated
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
   OtherThe reaction mixture was quenched with 13 mL 2M NH3 in methanol
7. 7
   OtherThe volatiles were removed in vacuo
8. 8
   Otherthe resulting crude oil was purified by silica gel flash chromatography ethyl acetate/n-hexane (10:90)

Procedure

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).

Source