Triethylamine → HCID 86597427, compound

HRID 242560Notes

Reaction equation

HRID 242560 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:29])C=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:12]([O:29]2)[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 157514251,1-Dimethylethyl 4-(4-chlorophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate

Product 1

HCID 86597427HCID 86597427, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-Chloro-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (3.8 g, 13 mmol) in CH2Cl2 (50 mL) was added 3-chloroperbenzoic acid (3.8 g, 17.0 mmol) and triethylamine (3.6 mL, 20 mmol). The solution was stirred at room temperature for about 4 hours. A white precipitate was observed. The reaction was quenched with aqueous sodium bicarbonate, extracted with CH2Cl2, and the organic layers were evaporated in vacuo. The residue was purified by flash chromatography on silica gel (35 g SiO2, gradient elution from 100% hexane to 100% ethyl acetate) to yield the title compound as a colorless oil.

Workup

  1. customThe reaction was quenched with aqueous sodium bicarbonate
  2. extractionextracted with CH2Cl2
  3. customthe organic layers were evaporated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel (35 g SiO2, gradient elution from 100% hexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-8ab7cb3b9a484269ac2421530f4e3f02
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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