Triethylamine → HCID 66750712, compound

HRID 504142Notes

Reaction equation

HRID 504142 reaction equation
Cl.[CH2:2]([O:9][C:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][NH:13]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[F:25][C:26]([F:38])([F:37])[C:27]1[CH:28]=[C:29]([S:33](Cl)(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1>>[CH2:2]([O:9][C:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]1[S:33]([C:29]1[CH:30]=[CH:31][CH:32]=[C:27]([C:26]([F:25])([F:37])[F:38])[CH:28]=1)(=[O:35])=[O:34])=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 66751061HCID 66751061, compound

Product 1

HCID 66750712HCID 66750712, compoundYield 100%

Procedure

To 4.0 g (15.64 mmol or millimoles) of (S)-piperidine-2-carboxylic acid benzyl ester hydrochloride and 3.15 g (31.28 mmol) of triethylamine in (200 ml) was added 4.21 g (17.20 mmol) of 3-trifluoromethylbenzenesulfonyl chloride. The mixture was stirred at room temperature for 1 hour. The reaction mixture was then washed with water, brine and dried (sodium sulfate). Chromatography on silica gel, eluting with dichloromethane provided 6.7 g (15.64 mmol) of (S)-1-(3-Trifluoromethyl-benzenesulfonyl)-piperidine-2-carboxylic acid benzyl ester. LCMS (M+H): m/z 428, retention time 3.9 min.

Workup

  1. washThe reaction mixture was then washed with water, brine
  2. dry with materialdried (sodium sulfate)
  3. washChromatography on silica gel, eluting with dichloromethane

Sources & evidence

ORD record
ord-4325fb2c65724ba9b78d0bf644ed7101
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

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