Butyl iodide → 2-Butyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

HRID 661512

Reaktionsgleichung

[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.I[CH2:28][CH2:29][CH2:30][CH3:31]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a stirred solution of pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (3.00 g, 13.1 mmol) in THF (50 mL) at −78° C. and under nitrogen was added LHMDS (14.4 mL of 1.0 M solution in THF, 14.4 mmol) dropwise. After 30 minutes, a solution of 1-iodobutane (2.23 mL, 19.7 mmol) in THF (1 mL) was added dropwise. The reaction mixture was stirred for 30 minutes at −78° C., warmed to ambient temperature over 90 minutes, then quenched by the addition of saturated aqueous NH4Cl and extracted with EtOAc. The combined extracts were washed with saturated aqueous NaHCO3 and brine then dried (MgSO4), filtered and concentrated in vacuo to a yellow oil (4.5 g). Purification by chromatography (silica, 10% EtOAc in hexanes) gave 2-butyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (2.57 g, 9.01 mmol, 69%) as a clear colourless oil.

Aufarbeitung

temperaturewarmed to ambient temperature over 90 minutes
customquenched by the addition of saturated aqueous NH4Cl
extractionextracted with EtOAc
washThe combined extracts were washed with saturated aqueous NaHCO3 and brine
dry with materialthen dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo to a yellow oil (4.5 g)
customPurification by chromatography (silica, 10% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-eff591d2f427453ebf38d31f7e602612
Quelldatensatz: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08084623B2

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