Trifluoroacetic acid → HCID 86660373, compound

To an ice-cold solution of tert-butyl 4-(cyclopropylmethylsulfonyl)piperidine-1-carboxylate (53, 0.9 g, 2.96 mmol) in CH2Cl2 (15 mL) was added TFA (3.0 mL). The mixture stirred at room temperature and stirred for 3 h and was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (25 mL) and the organic layer was washed with saturated NaHCO3 solution (10 mL), H2O (15 mL) brine (15 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed over silica gel (Isco CombiFlash Companion unit, 40 g Redisep column, 30% to 50% EtOAc in hexanes) to give 4-(cyclopropylmethylsulfonyl)piperidine as a white foam (54, 0.38 g, 63%); 1H NMR (300 MHz, MeOH-d4): δ 3.27-3.24 (m, 1H), 3.23-3.12 (m, 2H), 2.99 (d, J=7.2 Hz, 2H), 2.63 (dt, J=2.4, 12.0 Hz, 2H), 2.10-2.01 (m, 2H), 1.77-1.60 (m, 2H), 1.27-1.14 (m, 1H), 0.83-0.64 (m, 2H), 0.45-0.39 (m, 2H);

1. stirringstirred for 3 h
2. concentrationwas concentrated under reduced pressure
3. dissolutionThe residue was dissolved in CH2Cl2 (25 mL)
4. washthe organic layer was washed with saturated NaHCO3 solution (10 mL), H2O (15 mL) brine (15 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was chromatographed over silica gel (Isco CombiFlash Companion unit, 40 g Redisep column, 30% to 50% EtOAc in hexanes)

ORD record

ord-41a0f116f0824e9d84c4dbf996c7469f

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045445B2