Triethylamine → HCID 86656365, compound

HRID 1942522Notes

Reaction equation

HRID 1942522 reaction equation
[NH2:1][C@@H:2]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:3]1.C(N(CC)CC)C.[N+:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[S:37](Cl)(=[O:39])=[O:38])([O-:30])=[O:29].[Cl-].[NH4+]>C(Cl)Cl>[N+:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[S:37]([NH:1][C@@H:2]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:3]1)(=[O:39])=[O:38])([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 25517Ammonium ChlorideHCID 25324004HCID 25324004, compound

Product 1

HCID 86656365HCID 86656365, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (3R,4R)-3-amino-4-phenylpiperidine-1-carboxylate (124 mg) was dissolved in methylene chloride (2 ml), and thereto were added triethylamine (125 μl) and 2-nitrobenzene sulfonyl chloride (109 mg) at 0° C., and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (the developing solvent: hexane/ethyl acetate=1/1) to give the title compound (202 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-ed83afafcb294faba7e733c4f2512e34
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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