(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → HCID 11023310, compound

HRID 1059699Notes

Reaction equation

HRID 1059699 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](O)([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>C1C=CC=CC=1.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 69842491HCID 69842491, compound

Product 1

HCID 11023310HCID 11023310, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

4-Hydroxy-4-quinolin-2-yl-piperidine-1-carboxylic acid tert-butyl ester (3.16 g, 9.61 mmol) and (methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt (5.00 g, 20.98 mmol) in benzene (60 mL) under N2 were refluxed for 3 hours. The solution was cooled to ambient temperature, diluted with water (50 mL) and the resulting mixture was stirred at ambient temperature for 10 minutes. The benzene layer was separated, washed with brine, dried over magnesium sulfate and concentrated onto silica gel; flash chromatography using an ethyl acetate/hexanes gradient gave 4-quinolin-2-yl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (1.65 g, 55%) as a yellow oil. 1H NMR CDCl3 δ 8.09 (d, J=9 Hz, 1H), 8.03 (d, J=8 Hz, 1H), 7.76 (d, J=8 Hz, 1H), 7.70-7.63 (m, 1H), 7.56 (d, J=9 Hz, 1H), 7.51-7.44 (m, 1H), 6.69-6.63 (m, 1H), 4.21-4.14 (m, 2H), 3.68 (t, J=6 Hz, 1H), 2.87-2.80 (m, 2H), 1.48 (s, 9H).

Workup

  1. customThe benzene layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated onto silica gel

Sources & evidence

ORD record
ord-9a61ad97e6914ac0b75ecea3aeb3e459
Source dataset
uspto-grants-2003_02
Patent number
US06521630B1

Reaction notes

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