Pentane → (2-Amino-5-methyl-phenyl)-cyclopropyl-methanone

Temperature

-10 °C

To a stirred solution of p-tolyl-carbamic acid tert-butyl ester (1.0 g, 4.8 mmol) in Et2O (10 mL) under a nitrogen atmosphere was added dropwise a 1.7 M solution of t-BuLi in pentan (6.5 mL, 11.1 mmol) over a 10-min period at −20° C. The mixture was stirred at −10° C. for 2.5 h and then cyclopropanecarboxylic acid methoxy-methyl-amide (0.92 g, 6.3 mmol) was added over 5 min. The mixture was allowed to warm to room temperature and stirred for further 1 h before it was quenched with aqueous NH4Cl. The organic phase was isolated and the aqueous phase was extracted with CH2Cl2, and the combined organic phases were dried and concentrated in vacuo. The crude material was dissolved CH2Cl2 (15 mL) and TFA (15 mL) and stirred at room temperature for 3 h. The reaction mixture was evaporated in vacuo, and added aqueous NaHCO3 to pH 7 and extracted with CH2Cl2. The combined organic phases were dried and concentrated in vacuo to give 0.80 g crude (2-amino-5-methyl-phenyl)-cyclopropyl-methanone as a yellow oil.

1. temperatureto warm to room temperature
2. stirringstirred for further 1 h before it
3. customwas quenched with aqueous NH4Cl
4. customThe organic phase was isolated
5. extractionthe aqueous phase was extracted with CH2Cl2
6. customthe combined organic phases were dried
7. concentrationconcentrated in vacuo
8. dissolutionThe crude material was dissolved CH2Cl2 (15 mL) and TFA (15 mL)
9. stirringstirred at room temperature for 3 h
10. customThe reaction mixture was evaporated in vacuo
11. additionadded aqueous NaHCO3 to pH 7
12. extractionextracted with CH2Cl2
13. customThe combined organic phases were dried
14. concentrationconcentrated in vacuo

ORD record

ord-4b4be39578504ec08ad789876d4b47f5

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07541373B2