Carbon tetrabromide → methyl (1R,3S)-3-(bromomethyl)cyclopentane-1-carboxylate

To a 0° C. solution of 99 (6.6 gm, 50 mmol, 1 equi.) in 60 mL of DCM was added triphenyl phosphine (60 mmol, 1.2 equi, 15.72 gm) followed by carbon tetrabromide (60 mmol, 1.2 equi. 19.86 gm). The reaction mixture was stirred overnight allowing the temperature to rise to room temperature. Reaction was concentrated to dryness and the residue was diluted with ether/DCM (1:1, 20 ml) and filtered through a pad of celite. The filtrate was concentrated to dryness and the residue was purified by silica gel chromatography with (5% to 20% EtOAc in hexanes) to provide 3.5 g of (1R,3S)-methyl 3-(bromomethyl)cyclopentanecarboxylate 100.

1. customto rise to room temperature
2. customReaction
3. concentrationwas concentrated to dryness
4. additionthe residue was diluted with ether/DCM (1:1, 20 ml)
5. filtrationfiltered through a pad of celite
6. concentrationThe filtrate was concentrated to dryness
7. customthe residue was purified by silica gel chromatography with (5% to 20% EtOAc in hexanes)

ORD record

ord-0647b60b1b9a49d6853e74140732664d

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859776B2