반응 #50024

반응 방정식

L-proline methyl ester hydrochloride

hydrogen

sodium acetate

formaldehyde

→

crude product

수율 77.0%

N-Methyl Proline Methyl Ester

수율 77.0%

반응 조건

후처리

1. 1
   기타Upon completion of the reaction
2. 2
   농축the methanolic solution was concentrated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in 10% aq. HCl (60 mL)
4. 4
   세척washed with ether (3×100 mL)
5. 5
   추출extracted with methylene chloride (3×75 mL)
6. 6
   건조The combined methylene chloride layers were dried (MgSO4)
7. 7
   농축concentrated

실험 절차

A 10.42 g (62.92 mmol) sample of L-proline methyl ester hydrochloride (Aldrich Chemical Co.) was reductively methylated over 2.5 g of 10% Pd/C under 4 Atm of hydrogen in a solution containing 20 g of sodium acetate and 49.5 mL of 37% aqueous formaldehyde for 48 hours. Upon completion of the reaction, the methanolic solution was concentrated and the residue was dissolved in 10% aq. HCl (60 mL) and washed with ether (3×100 mL), then the aqueous layer was adjusted to pH ~12 with K2CO3 (solid) and extracted with methylene chloride (3×75 mL). The combined methylene chloride layers were dried (MgSO4) and concentrated to afford the crude product as a clear oil (16.6 g, 77% yield).

출처