반응 #48312

반응 방정식

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

용매

ether

반응 조건

후처리

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

실험 절차

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).

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