(S)-1-Boc-pyrrolidine-3-carboxylic acid methyl ester

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(S)-1-Boc-pyrrolidine-3-carboxylic acid methyl ester Basic information
Product Name:(S)-1-Boc-pyrrolidine-3-carboxylic acid methyl ester
Synonyms:(S)-1-BOC-PYRROLIDINE-3-CARBOXYLIC ACID METHYL ESTER;(S)-1-tert-Butoxycarbonyl-pyrrolidine-3-carboxylic acid methyl ester;(R)-1-tert-butyl 3-methyl pyrrolidine-1,3-dicarboxylate;(R)-1-tert-butyl 3-methyl pyrrolidine-;(S)-1-1-Boc-pyrrolidine-3-carboxylic acid methyl ester;(S)-1-Boc-pyrrolidine-1,3-dicarboxylate;(S)-1-tert-butyl 3-Methyl pyrrolidine-1,3-dicarboxylate;(S)-Methyl 1-Boc-pyrrolidine-3-carboxylate
CAS:313706-15-9
MF:C11H19NO4
MW:229.27
EINECS:
Product Categories:Pyrrole&Pyrrolidine&Pyrroline
Mol File:313706-15-9.mol
(S)-1-Boc-pyrrolidine-3-carboxylic acid methyl ester Structure
(S)-1-Boc-pyrrolidine-3-carboxylic acid methyl ester Chemical Properties
Boiling point 288.6±33.0 °C(Predicted)
density 1.120±0.06 g/cm3(Predicted)
storage temp. 2-8°C
pka-2.65±0.40(Predicted)
AppearanceColorless to light yellow Liquid
CAS DataBase Reference313706-15-9
Safety Information
MSDS Information
(S)-1-Boc-pyrrolidine-3-carboxylic acid methyl ester Usage And Synthesis
Synthesis
(3S)-1-(tert-Butoxycarbonyl)-3-pyrrolidinecarboxylic acid

140148-70-5

Iodomethane

74-88-4

(S)-1-Boc-pyrrolidine-3-carboxylic acid methyl ester

313706-15-9

To a solution of (S)-1-BOC-pyrrolidine-3-carboxylic acid (863 mg, 4.01 mmol) and K2CO3 (829 mg, 6.00 mmol) in anhydrous DMF (8 mL) was added iodomethane (300 μL, 4.82 mmol). The reaction mixture was stirred at room temperature for 4 hours. After completion of the reaction, water was added and extracted three times with ether (Et2O). The organic phases were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by fast column chromatography (eluent: n-hexane/ethyl acetate = 3:1) to afford the target product (S)-1-Boc-3-carboxypyrrolidinium methyl ester (916 mg, 100%) as a colorless oil. The product was confirmed by 1H NMR (400 MHz, CDCl3): δ 3.70 (3H, s), 3.65-3.28 (4H, m), 3.10-2.98 (1H, m), 2.18-2.05 (2H, m), 1.45 (9H, s). lRMS (ESI, [M + Na]+) showed the molecular ion peak as 252.1.

References[1] Tetrahedron, 2012, vol. 68, # 23, p. 4418 - 4428
[2] Patent: WO2013/25733, 2013, A1. Location in patent: Paragraph 0769
[3] Patent: WO2016/112088, 2016, A1. Location in patent: Paragraph 0749
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