Methyl iodide → 1-benzyloxycarbonyl-3-(R)-[1-[N-(tert-butoxycarbonyl)-N-(methyl)Amino]Cyclopropyl]Pyrrolidine

Temperature

80 °C

1-benzyloxycarbonyl-3-(R)-[1-(tert-butoxycarbonylamino)cyclopropyl]pyrrolidine (1.40 g, 3.89 mmol), N,N′-dimethylformamide (7 ml), silver oxide (9.0 g, 39 mmol) and methyl iodide (24 ml, 389 mmol) were placed in a shaded and sealed tube, and this mixture was stirred for 13 hours in an oil bath of 80° C. The reaction solution was then filtered through cellite (ethyl acetate washing) and the filtrate was then diluted with ethyl acetate (100 ml). The organic layer was then washed with water (50 ml×3) and saturated saline solution (50 ml) in that order, and dried over anhydrous sodium sulfate. After filtering, the filtrate was concentrated under a reduced pressure, the concentrate was applied to a silica gel chromatography, and 1.31 g (89%) of the title compound was obtained in the form of a pale-yellow syrup an n-hexane:ethyl acetate=2:1 eluate. The instrumental analysis data for this resulting compound agreed with the data indicated in PCT/JP96/00208.

1. customsealed tube
2. filtrationThe reaction solution was then filtered through cellite (ethyl acetate washing)
3. additionthe filtrate was then diluted with ethyl acetate (100 ml)
4. washThe organic layer was then washed with water (50 ml×3) and saturated saline solution (50 ml) in that order
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationAfter filtering
7. concentrationthe filtrate was concentrated under a reduced pressure

ORD record

ord-5ce6f1ce1a34463fa179b1935fa51144

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07902226B2