Triethylamine → HCID 60345718, compound

HRID 1776188Notes

Reaction equation

HRID 1776188 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH:6]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:7]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][S:2]([N:6]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:7]1[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27517Ethyl piperidine-2-carboxylateHCID 31297Methanesulfonyl chloride

Product 1

HCID 60345718HCID 60345718, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (4.0 g, 35 mmol) was slowly added to a stirring solution of ethyl pipecolinate, (5.5 g, 35 mmol) and triethylamine (4.9 mL, 35 mmol) in anhydrous methylene chloride (88 mL). The reaction was stirred overnight at ambient temperature and then diluted with ethyl acetate. The organic layer was successively washed with water, twice with 1N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride solutions, dried (anhydrous sodium sulfate), and filtered. The solution was concentrated under reduced pressure to give the desired product as a tan liquid (6.9 g, 84%). 1H NMR (CDCl3, 300 MHz) δ 4.72-4.71 (br d, 1H, J=3.6 Hz), 4.24-4.16 (qd, 2H, J=6.9, 2.6 Hz), 3.74-3.68 (m, 1H), 3.22-3.13 (td, 1H, J=12.3, 3.0 Hz), 2.93 (s, 3H), 2.31-2.25 (m, 1H), 1.83-1.51 (m, 5H), 1.32-1.27 (td, 3H, J=7.0, 0.6 Hz), 3.52-3.42 (m, 1H), 3.01 (s, 3H), 2.32-2.22 (m, 1H), 2.11-1.98 (m, 3H). ESI (m/z): 235.9 (M+H).

Workup

  1. washThe organic layer was successively washed with water, twice with 1N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride solutions
  2. dry with materialdried (anhydrous sodium sulfate)
  3. filtrationfiltered
  4. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-25168d1c8dde4ab592d70480f0829f0c
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

Loading…