(2S)-1-Methyl-2-azetidinecarboxylic acid synthesis
- Product Name:(2S)-1-Methyl-2-azetidinecarboxylic acid
- CAS Number:255882-95-2
- Molecular formula:C5H9NO2
- Molecular Weight:115.13
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Yield:-
Reaction Conditions:
with hydrogen;palladium 10% on activated carbon in methanol;water for 19 h;
Steps:
4
N-methyl-L-azetidine-2-carboxilic acid To a suspension of L-azetidine-2-carboxylic acid (290 mg, 2 87 mmol, 1 equiv) in MeOH (3.6 mL), was added aqueous formaldehyde solution (37%, 235 μL, 3.15 mmol, 1. 1 equiv) and palladium on carbon (10%, 76 mg). The flask was fitted with a septum and evacuated and back-filled three times with hydrogen gas. The reaction was stirred under an atmosphere (balloon) of hydrogen gas for 19 h, and was filtered through celite to remove the palladium catalyst. The resulting solution was concentrated under reduced pressure, concentrated from toluene three times and dried under vacuum to afford N-methyl-L-azetidine-2-carboxilic acid: 1II NMR (400 MHz, CD3OD) δ 4.50 (t, J= 9.5 Hz, 1 H), 3.96 (dt, J = 4.3, 9.8 Hz, I H), 3.81 (q, J = 9.8 Hz, 1 H), 2.86 (s, 3 H), 2.71-2.60 (m, 1 H), 2.50-2.38 (m, 1 H).
References:
Location in patent:Page/Page column 96-97