Reaction #1178425

Reaction equation

[1-(methoxy-methyl-carbamoyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester

TFA

→

2-amino-N-methoxy-2,N-dimethyl-propionamide

Yield 176.0%

Solvents

TFA CH2Cl2

Conditions

Workup

1. 1
   OtherRemoval of the solvent

Procedure

The Boc-protected Weinreb amide, [1-(methoxy-methyl-carbamoyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester, (1.1 g, 4.47 mmol), was taken up in TFA/CH2Cl2 (1:1, 50 mL) and stirred for 20 min. Removal of the solvent left 2-amino-N-methoxy-2,N-dimethyl-propionamide (1.15 g, 99%, quantitative yield) as its TFA salt. 1H NMR (200 MHz, CD3OD) δ (ppm): 1.63 (s, 6H), 3.25 (s, 3H), 3.78 (s, 3H). MS (ESI, positive ion): m/z 147.3 (M+1)+.

Source