N,N,N',N'-Tetramethylethylenediamine → Tert-butyl 2-phenylpyrrolidine-1-carboxylate

To a solution of tetramethylethylenediamine (0.83 mL, 5.47 mmol) and n-BuLi (1.6 M/hexane, 3.31 mL, 5.3 mmol) cooled at −78° was added dropwise N-Boc-N-benzyl-3-chloropropylamine (1.0 g, 3.53 mmol) in THF. The resulting yellow solution was stirred at −78° for 5 h. The reaction mixture was then quenched with aqueous NH4Cl (20 mL) and diluted with Et2O (150 mL), the layers were separated and the aqueous layer was extracted twice with Et2O. The combined organic phases were washed with H2O and brine, dried (MgSO4), filtered and concentrated. The resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane) to give 2-phenylpyrrolidine-1-carboxylic acid tert-butyl ester (0.57 g, 65% yield).

1. customThe reaction mixture was then quenched with aqueous NH4Cl (20 mL)
2. additiondiluted with Et2O (150 mL)
3. customthe layers were separated
4. extractionthe aqueous layer was extracted twice with Et2O
5. washThe combined organic phases were washed with H2O and brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe resulting yellow oil was purified by flash chromatography (SiO2, 10% EtOAc-hexane)

ORD record

ord-f7cffdb1601b4147957e2c4ae980b705

Source dataset

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06211170B1