(2S,4S)-4-(2-Propen-1-yl)-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl ester synthesis

6synthesis methods

Product Name:(2S,4S)-4-(2-Propen-1-yl)-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl ester
CAS Number:934470-80-1
Molecular formula:C13H21NO4
Molecular Weight:255.31

1,2-Pyrrolidinedicarboxylic acid, 4-(2-propen-1-yl)-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,4S)-

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(2S,4S)-4-(2-Propen-1-yl)-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl ester

934470-80-1
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Yield:934470-80-1 98%

Reaction Conditions:

in tetrahydrofuran;

Steps:

1.C C)

C)
(2S,4S)-4-Allyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid
To a solution of (2S,4S)-1-tert-butyl 2-methyl 4-allylpyrrolidine-1,2-dicarboxylate (5.5 g, 20.42 mmol) in THF (50 mL) and MeOH (10 mL) was added aq. LiOH (1M, 30.6 mL, 30.6 mmol).
The resulting mixture was stirred at room temperature for 5 h before it was cooled to 0° C., acidified with 1 N HCl to pH 3-4, and extracted with DCM (3*).
The combined organic extracts were dried over MgSO₄ and concentrated in vacuo to give the title compound (5.11 g, 98%) as a white solid. MS (ESI⁺) m/z 288.3 (M+Na)⁺.

References:

US2014/135270,2014,A1 Location in patent:Page/Page column

1,2-Pyrrolidinedicarboxylic acid, 5-oxo-4-(2-propen-1-yl)-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,4S)-

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24424-99-5 Synthesis

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L-Proline, 5-oxo-4-(2-propen-1-yl)-, methyl ester, (4S)-

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References