ChemicalBook CAS DataBase List (S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid

(S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid synthesis

5synthesis methods

Product Name:(S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid
CAS Number:1001353-87-2
Molecular formula:C12H21NO4
Molecular Weight:243.3

To a solution of 1-(tert-butyl) 2-methyl (S)-4,4-dimethylpyrrolidine-1,2-dicarboxylate (4.85 g, 18.86 mmol) in THF (40 mL) was dropwise added lithium hydroxide monohydrate aqueous solution (1.5 g, 20 mL) at 0 °C. At the end of the addition, the mixture was stirred at rt for 2.0 h. After that, the THF solvent was removed and 50 mL of water was added to the mixture. The resulting mixture was washed with EtOAc (30 mL x 3). The aqueous phase was adjusted to pH=1 with hydrochloric acid (1 M) and extracted with EtOAc (50 mL x 3). The combined organic layers were washed with brine, dried over anhydrous Na2S04, and concentrated in vacuo to give (S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid as a white solid (4.35 g, 95%).

(S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid

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Yield:1001353-87-2 95%

Reaction Conditions:

with lithium hydroxide monohydrate in water at 0 - 20; for 2 h;Inert atmosphere;Sealed tube;

Steps:

15.2 the preparation of compound 15-3

To a solution of compound 15-2 (4.85 g, 18.86 mmol) in THF (40 mL) was added lithium hydroxide monohydrate aqueous solution (1.5 g, 20 mL) dropwise at 0 °C. At the end of the addition, the mixture was stirred at rt for 2.0 hrs. After the reaction was completed, the THF solvent was removed and 50 mL of water was added to the mixture. The resulting mixture was washed with EtOAc (30 mL x 3). The aqueous phase was adjusted to pH 1 with hydrochloric acid (1 M) and extracted with EtOAc (50 mL x 3). The combined organic layers were washed with brine, dried over anhydrous Na₂S0₄ and concentrated in vacuo to give the title compound as a white solid (4.35 g, 95%). The compound was characterized by the following spectroscopic data: MS (ESI, pos.ion) mlz: 244.5 [M+H]⁺; 'H NMR (400 MHz, CD₃OD) δ (ppm): 4.34-4.31 (m, 1H), 3.28-3.22 (m, 1H), 3.20-3.13 (m, 1H), 2.23-2.18 (m, 1H), 1.85-1.80 (m, 1H), 1.46 (s, 9H), 1.01-0.99 (m, 3H), 0.86-0.84 (m, 3H).

References:

WO2014/82380,2014,A1 Location in patent:Paragraph 00460; 00462