1,2-Pyrrolidinedicarboxylic acid, 4,4-diMethyl-, 1-(1,1-diMethylethyl) ester, (2R)- synthesis

8synthesis methods

Product Name:1,2-Pyrrolidinedicarboxylic acid, 4,4-diMethyl-, 1-(1,1-diMethylethyl) ester, (2R)-
CAS Number:1417743-49-7
Molecular formula:C12H21NO4
Molecular Weight:243.3

(R)-2-benzyl-1-(tert-butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid

1417743-48-6
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1,2-Pyrrolidinedicarboxylic acid, 4,4-diMethyl-, 1-(1,1-diMethylethyl) ester, (2R)-

1417743-49-7
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Yield:1417743-49-7 84 mg

Reaction Conditions:

with lithium hydroxide monohydrate in 1,4-dioxane;water at 20; for 18 h;

Steps:

41 (H)-1-(iefi-butoxycarbonyl)-4,4-dimethylpyrrolidine-2-

To a mixture of (f?)-2-benzyl 1 -feri-butyl 4,4-dimethylpyrrolidine-l ,2-dicarboxylate (D40) (198 mg, 0.59 mmol) in dioxan/water (4/4ml), LiOH.H₂0 (100 mg, 2.37 mmol) was added and the mixture was left stirring at RT for 18hrs. Organic solvent was evaporated off and the reaction mixture was diluted with water (8 ml), washed with Et₂O (2x10ml), acidified with acetic acid to pH~4-5 and extracted with Et₂O (3x10ml). The organic phases were collected, dried over Na₂SO₄ and evaporated in vacuo to afford the title compound (D41) (84 mg). MS: (ES/+) m/z: 144.1 [MH-Boc⁺] C12H21 NO4 requires 243.15 ¹ H NMR (400MHz, CHCI3-d) δ (ppm): 4.51 - 4.20 (m, 1 H), 3.45 - 3.05 (m, 2 H), 2.32 - 1 .81 (m, 2 H), 1 .62 - 1 .39 (m, 9 H), 1 .19 - 1 .03 (m, 6 H)

References:

WO2013/4290,2013,A1 Location in patent:Page/Page column 63

66673-40-3 Synthesis