(2S,5S)-N-Boc-5-methylpyrrolidine-2-carboxylic acid

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(2S,5S)-N-Boc-5-methylpyrrolidine-2-carboxylic acid manufacturers

(2S,5S)-N-Boc-5-methylpyrrolidine-2-carboxylic acid Basic information
Product Name:(2S,5S)-N-Boc-5-methylpyrrolidine-2-carboxylic acid
Synonyms:(2S,5S)-N-Boc-5-Methylpyrrolidine-2-carboxylic aci;GS-5817 interMediate;2. (2S,5S)-1-(tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid;(2S,5S)-N-Boc-5-methylpyrrolidine-2-carboxylic acid(2S,5S)-N-Boc-5-methylpyrrolidine-2-carboxylic acid;(2S,5S)-5-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;(2S,5S)-Boc-5-methylpyrrolidine-2-carboxylic acid;Boc-cis-5-methyl-Pro-OH;cis-5-Methyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
CAS:334769-80-1
MF:C11H19NO4
MW:229.27
EINECS:
Product Categories:
Mol File:334769-80-1.mol
(2S,5S)-N-Boc-5-methylpyrrolidine-2-carboxylic acid Structure
(2S,5S)-N-Boc-5-methylpyrrolidine-2-carboxylic acid Chemical Properties
Boiling point 343.2±35.0 °C(Predicted)
density 1.150
storage temp. 2-8°C
pka4.02±0.40(Predicted)
AppearanceWhite to off-white Solid
Safety Information
MSDS Information
(2S,5S)-N-Boc-5-methylpyrrolidine-2-carboxylic acid Usage And Synthesis
Synthesis
(2S,5S)-1-tert-butyl 2-ethyl 5-methylpyrrolidine-1,2-dicarboxylate

676560-83-1

(2S,5S)-N-Boc-5-methylpyrrolidine-2-carboxylic acid

334769-80-1

The general procedure for the synthesis of (2S,5S)-N-Boc-5-methylpyrrolidine-2-carboxylic acid from the compound (CAS: 676560-83-1) is as follows: 1. ethyl (2S,5S)-1-(tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylate (6.46 g, 25.1 mmol) was dissolved in ethanol (20 mL). 2. Lithium hydroxide monohydrate (2.11 g, 50.2 mmol) and deionized water (12 mL) were added to the above solution. 3. The reaction mixture was stirred at room temperature for 16 hours. 4. 4. Upon completion of the reaction, the mixture was partitioned between ethyl acetate and a 1:1 mixture of saturated aqueous sodium chloride solution and 1N hydrochloric acid. 5. The aqueous layer was separated and extracted again with ethyl acetate. 6. Combine all organic layers and dry with anhydrous sodium sulfate. 7. Vacuum removal of the solvent afforded (2S,5S)-1-(tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid as a white solid (quantitative yield), which was used directly in the next reaction without further purification.

References[1] Patent: US2014/178336, 2014, A1. Location in patent: Paragraph 0252
[2] Patent: US2015/361087, 2015, A1. Location in patent: Paragraph 0311; 0316
[3] Patent: WO2015/110048, 2015, A1. Location in patent: Paragraph 00165
[4] Patent: US2017/44140, 2017, A1. Location in patent: Paragraph 0218; 0231; 0232; 0233
[5] Journal of Medicinal Chemistry, 2006, vol. 49, # 12, p. 3520 - 3535
(2S,5S)-N-Boc-5-methylpyrrolidine-2-carboxylic acid Preparation Products And Raw materials
Raw materials(2S,5S)-1-tert-butyl 2-ethyl 5-methylpyrrolidine-1,2-dicarboxylate-->Di-tert-butyl dicarbonate-->(2S,5S)-5-methylpyrrolidine-2-carboxylic acid-->Water-->Lithium hydroxide monohydrate-->Ethanol
Tag:(2S,5S)-N-Boc-5-methylpyrrolidine-2-carboxylic acid(334769-80-1) Related Product Information
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