tert-Butyl-(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-formylpyrrolidine-1-carboxylate → (2R,3R)-3-(tert-Butyl-dimethylsilanyloxy)-2-[(1S)-(1-hydroxy-2-methylpropyl)]pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 751143

Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@H:9]1[CH:21]=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:23]([Mg]Cl)([CH3:25])[CH3:24]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[C@H:9]1[C@@H:21]([OH:22])[CH:23]([CH3:25])[CH3:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: -60 °C

Versuchsvorschrift

To 51C (6.50 g, 19.8 mmol) in THF (100 mL) at −78° C. was added a 2M THF solution of isopropylmagnesium chloride (30.0 mL, 60.0 mmol) over 20 min. The cold bath was removed and the reaction was stirred for 1 h. The reaction was then cooled to −60° C. and was quenched with saturated aqueous ammonium chloride. After warming to rt, the whole was diluted with EtOAc. The layers were separated and the organic layer washed with water and brine, then dried (MgSO4), filtered and concentrated. The resulting residue was purified via flash chromatography eluting with 20% EtOAc/hexane to provide the title compound (5.90 g).

Aufarbeitung

customThe cold bath was removed
customwas quenched with saturated aqueous ammonium chloride
temperatureAfter warming to rt
additionthe whole was diluted with EtOAc
customThe layers were separated
washthe organic layer washed with water and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe resulting residue was purified via flash chromatography
washeluting with 20% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag: ord-69203770de73429e89a5770bc9604a89
Quelldatensatz: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07405234B2

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