Diisopropylethylamine → 2-{(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(3R,4S)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-5-chloro-pyridine

Temperature

100 °C

To a solution of 2-[(R)-1-[(3R,4S)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-5-chloro-pyridine 570 mg (0.96 mmol) dissolved in toluene (4 mL) was added 0.31 mL (2.89 mmol) of 1-chloroethyl chloroformate and 0.491 mL (2.89 mmol) of Hunig base subsequently, and the mixture was heated at 100° C. for 40 minutes, then concentrated in vaccuo. The residue was dissolved in methanol (5 mL) and stirred at room temperature over night. The mixture was concentrated in vaccuo and diluted with ethyl acetate, then washed with aq. sodium bicarbonate solution twice. The separated organic layer was dried over sodium sulfate and concentrated in vaccuo after filtration yielded 0.40 g (83%) of the title compound as a light brown oil. ES-MS m/e: 501.2 (M+H+).

1. concentrationconcentrated in vaccuo
2. dissolutionThe residue was dissolved in methanol (5 mL)
3. concentrationThe mixture was concentrated in vaccuo
4. additiondiluted with ethyl acetate
5. washwashed with aq. sodium bicarbonate solution twice
6. dry with materialThe separated organic layer was dried over sodium sulfate
7. concentrationconcentrated in vaccuo
8. filtrationafter filtration

ORD record

ord-e6c1bdb839724146a0aa7d141cce15a8

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08012998B2