trans-4-Hydroxy-L-proline methyl ester hydrochloride synthesis
- Product Name:trans-4-Hydroxy-L-proline methyl ester hydrochloride
- CAS Number:40216-83-9
- Molecular formula:C6H12ClNO3
- Molecular Weight:181.62
67-56-1
32968-78-8
40216-83-9
The general procedure for synthesizing trans-4-hydroxy-L-proline methyl ester hydrochloride from methanol and trans-4-hydroxy-L-proline hydrochloride is as follows: Example 1: (2S,4R)-4-hydroxy-2-pyrrolidine carboxylic acid hydrochloride (1.0 g, 7.6 mmol) was dissolved in methanol (25 mL) and cooled to 0°C. Thionyl chloride (0.83 mL, 11.4 mmol) was added slowly under stirring. The reaction mixture was gradually warmed to room temperature and subsequently heated to reflux overnight. After completion of the reaction, it was cooled to room temperature and the reaction mixture was concentrated to dryness under reduced pressure to afford trans-4-hydroxy-L-proline methyl ester hydrochloride (1.2 g, 92% yield) in white solid form. The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6).
67-56-1
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40216-83-9
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Yield:40216-83-9 99%
Reaction Conditions:
with hydrogenchloride at 20; for 12 h;
Steps:
Compound 20r (2 g, 8.6 mmol) was taken up with a solution of HC1 (g) in methanol (4 M, 40 mL). The mixture was stirred at ambient temperature for 12 hrs. After that, the reaction mixture was concentrated under reduced pressure to afford compound 20s (1.6 g, yield 99%) as a white solid.
References:
INTERMUNE, INC.;BUCKMAN, Brad;NICHOLAS, John, B.;SEREBRYANY, Vladimir;SEIWERT, Scott, D. WO2012/37259, 2012, A1 Location in patent:Page/Page column 74
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32968-78-8
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40216-83-9
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74844-91-0
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40216-83-9
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