(S)-3-(2-AMino-acetylaMino)-pyrrolidine-1-carboxylic acid tert-butyl ester synthesis

7synthesis methods

Product Name:(S)-3-(2-AMino-acetylaMino)-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS Number:193269-79-3
Molecular formula:C11H21N3O3
Molecular Weight:243.3

1-Pyrrolidinecarboxylic acid, 3-[(2-bromoacetyl)amino]-, 1,1-dimethylethyl ester, (3S)-

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(S)-3-(2-AMino-acetylaMino)-pyrrolidine-1-carboxylic acid tert-butyl ester

193269-79-3
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Yield:193269-79-3 96.8%

Reaction Conditions:

with ammonium hydroxide;sodium iodide in methanol;water at 20; for 48 h;

Steps:

31.2

Step 2:To a solution of compound 157 (6.0 g, 19.53 mmol) in MeOH (110 mL) was added Nal (8.78 g, 58.6 mmol) and 28% aqueous NH₄OH (1 10 mL). The resulting mixture was stirred at room temperature for 48 h. The mixture was evaporated under reduced pressure to dryness. The residue was purified by silica gel flash chromatography eluting with ACN to give 4.6 g of the desired product 158 (96.8%). ¹H NMR (CDCI₃, 400 MHz): δ 8.38 and 8.28 (s + s, 1H), 7.64 (br s, 2H), 4.51 - 4.42 (m, 1H), 4.25 - 4.00 (m, 2H), 3.66 - 3.34 (m, 4H), 2.20 - 2.00 (m, 2H), 1.41 (s, 9H).

References:

WO2011/160020,2011,A2 Location in patent:Page/Page column 112-113

335280-33-6 Synthesis