反应 #48312

反应方程式

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

溶剂

ether

反应条件

后处理

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

实验过程

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).

来源