Ammonium formate → 3-Amino-1-(2-trimethylsilylethoxymethyl)pyrrolidin-2-one

Temperature

55 °C

A suspension of 10% Pd/C paste (1 g, 0.4400 mmol), benzyl N-[2-oxo-1-(2-trimethylsilylethoxy-methyl)-pyrrolidin-3-yl]carbamate (which may be prepared as described in Description 40) (7.2 g, 19.8 mmol) and ammonium formate (3.7 g, 58.6 mmol) in methanol (400 mL) was heated at a block temperature of 55° C. under N2 for 2 hours. The reaction was cooled to ambient temperature and filtered through Celite under N2 and washed with MeOH (2×25 mL). The filtrate was evaporated to a colourless oil. The oil was partitioned between DCM (75 mL) and water (75 mL). The latter was re-extracted with DCM (5×50 mL) then DCM/MeOH (9:1) (2×50 mL) and the combined organic extracts were dried (Na2SO4) and evaporated to a colourless oil, which was dried at room temperature under vacuum for 14 hours to give 3-amino-1-(2-trimethylsilylethoxymethyl)pyrrolidin-2-one (D41) 2.7 g (11.7 mmol=59% yield);

1. temperatureThe reaction was cooled to ambient temperature
2. filtrationfiltered through Celite under N2
3. washwashed with MeOH (2×25 mL)
4. customThe filtrate was evaporated to a colourless oil
5. customThe oil was partitioned between DCM (75 mL) and water (75 mL)
6. extractionThe latter was re-extracted with DCM (5×50 mL)
7. dry with materialDCM/MeOH (9:1) (2×50 mL) and the combined organic extracts were dried (Na2SO4)
8. customevaporated to a colourless oil, which
9. customwas dried at room temperature under vacuum for 14 hours

ORD record

ord-8915a139aa95457e9f106a12be2871e2

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376436B2