Allyl bromide → Methyl 3-Allyl-1-Boc-pyrrolidine-3-carboxylate

HRID 1157202

Reaktionsgleichung

[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1)=[O:4].[Li+].[CH3:18][CH:19]([N-]C(C)C)[CH3:20].C(Br)C=C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1([CH2:20][CH:19]=[CH2:18])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1)=[O:4]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

Pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester 2 (see Example 1, Step 1) (4.58 g, 20 mmol) was dissolved in THF (100 mL) and cooled down to −78° C. in a dry ice-acetone bath. LDA (12 mL, 2.0 M, 24 mmol) was then added dropwise. The mixture was stirred at −78° C. for 1 hr. Allyl bromide (5.3 mL, 61 mmol) was added in neat. The reaction was allowed to warm to rt naturally and stirred for 24 hrs. It was then quenched with sat. NH4Cl solution, extracted with ethyl acetate 2×150 mL. The organic layer washed with brine, dried (MgSO4) and concentrated. The crude was purified on silica gel column using 4:1 hexanes/ethyl acetate to get the title compound (3.6 g) as a yellow oil. MS (292, MNa).

Aufarbeitung

temperatureto warm to rt naturally
stirringstirred for 24 hrs
customIt was then quenched with sat. NH4Cl solution
extractionextracted with ethyl acetate 2×150 mL
washThe organic layer washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe crude was purified on silica gel column

Quellen und Nachweise

ORD-Eintrag: ord-493d9e358cf6492d91b62b912362d12e
Quelldatensatz: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07807672B2

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