Tetrabutylammonium Fluoride → 2-(2-Benzyloxycarbonylamino-ethyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1965153Notizen

Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][Si](C(C)(C)C)(C)C)[CH2:10][CH:9]1[CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([OH:13])[CH2:10][CH:9]1[CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A solution containing 4 (5.9 g, 12.5 mmol) in anhydrous THF (100 mL) was cooled to 0° C. TBAF (1M/THF, 14 mL, 14.0 mmol) was added in one portion. After 5 h, the reaction mixture was diluted with EtOAc and washed successively with 1M HCl and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by flash silica gel chromatography (1:1 to 1:3 hexanes/EtOAc) to afford 4.1 g (91%) of 5. 1H NMR (CDCl3, 300 MHz): δ7.31 (m, 5H), 5.93 (m, 1H), 5.07 (m, 2H), 4.37 (m, 1H), 4.03 (m, 1H) 3.51-3.06 (m, 4H), 2.05 (m, 1H), 1.77 (m, 1H), 1.44 (s, 9H) ppm. Mass spectrum, m/z [365.2] (M+H)+.

Aufarbeitung

washwashed successively with 1M HCl and brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash silica gel chromatography (1:1 to 1:3 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag: ord-bfd391395e604ea4b58c95a895187d15
Quelldatensatz: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08415486B2

Notizen zur Reaktion

Wird geladen…