Reaktion #48312

Reaktionsgleichung

N-allyl-N-t-butylcarbamate (4′S)-6′-(bromo)-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]pyridin]-4′-amine

t-butyllithium

pivalaldehyde

→

N-allyl-N-t-butylcarbamate (4′S)-6′-(1-hydroxy-2,2-dimethylpropyl)-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]pyridin]-4′-amine

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONfreshly distilled)
2. 2
   workup.ADDITIONwas added
3. 3
   Sonstigehas been consumed
4. 4
   SonstigeThe reaction was quenched with sat'd NH4Cl
5. 5
   Sonstigethe organic layer separated
6. 6
   Sonstigechromatographed through a Redi-Sep® pre-packed silica gel column (120 g)
7. 7
   Wascheneluting with 0% to 30% EtOAc in hexane

Vorschrift

A solution of N-allyl-N-t-butylcarbamate-(4′S)-6′-(bromo)-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]pyridin]-4′-amine (4.12 g, 10.1 mmol) in ether (80 mL) was cooled to −78° C. and then t-butyllithium (12.5 ml, 21.3 mmol) was added and stirred for 15 minutes before the pivalaldehyde (3.80 ml, 35.0 mmol) (Note: freshly distilled) was added. After 5 minutes, LC-MS shows the starting material has been consumed. The reaction was quenched with sat'd NH4Cl and the organic layer separated. The organic layer was combined with previous trial reactions and adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (120 g), eluting with 0% to 30% EtOAc in hexane, to provide N-allyl-N-t-butylcarbamate-(4′S)-6′-(1-hydroxy-2,2-dimethylpropyl)-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]pyridin]-4′-amine as a yellow oil. MS m/z: 417 (M+1).

Quelle