Dimethyl Sulfoxide → HCID 57602860, compound

HRID 1788396Notes

Reaction equation

HRID 1788396 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH:22]=[C:21]([CH2:24][CH2:25][OH:26])[C:20]([CH3:28])([CH3:27])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH:22]=[C:21]([CH2:24][CH:25]=[O:26])[C:20]([CH3:28])([CH3:27])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 68826142HCID 68826142, compound

Product 1

HCID 57602860HCID 57602860, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of dimethylsulfoxide (1.1 mL, 15 mmol) in dichloromethane (5ml) was added to a cooled (−78° C.) solution of oxalyl chloride (0.67 mL, 7.5 mmol) in dichloromethane (50 mL) under an atmosphere of argon, and stirred for 10 minutes. Then a solution of 4-(2-hydroxyethyl)-3,3-dimethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (0.96 g, 3.7 mmol) in dichloromethane (5 mL) was added thereto and stirred for 15 minutes at −78° C. and subsequently for 45 minutes at −40° C. Then triethylamine (3.7 mL, 26.4 mmol) was added thereto and stirred for 30 minutes at room temperature. After the reaction was completed, saturated aqueous ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was washed with water three times and dried over anhydrous magnesium sulfate. After drying, it was filtered and the filtrate was concentrated under a reduced pressure. The residue was subjected to silica gel column chromatography (developing solvent, hexane:ethyl acetate=10:1 to 7:1) to obtain 0.39 g (yield 41.1%) of 3,3-dimethyl-4-(2-oxoethyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (VII-152). Its physical property is shown below.

Workup

  1. stirringstirred for 15 minutes at −78° C. and subsequently for 45 minutes at −40° C
  2. stirringstirred for 30 minutes at room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water three times
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter drying
  7. filtrationit was filtered
  8. concentrationthe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-c235919f9e6f457b9518331e938ac7b5
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

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