Sodium Chloride → 1-[4-(Tributylstannyl)-3,6-dihydropyridin-1(2H)-yl]ethan-1-one

HRID 2184801Notes

Reaction equation

HRID 2184801 reaction equation
S(Cl)(C)(=O)=O.[C:6]([N:9]1[CH2:14][CH2:13][C:12](O)([Sn:15]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][CH2:10]1)(=[O:8])[CH3:7].C(N(CC)CC)C.[Na+].[Cl-]>ClCCl>[C:6]([N:9]1[CH2:10][CH:11]=[C:12]([Sn:15]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:13][CH2:14]1)(=[O:8])[CH3:7]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 156368991-Acetyl-4-hydroxy-4-tributylstannyl-piperidine

Product 1

HCID 156368961-[4-(Tributylstannyl)-3,6-dihydropyridin-1(2H)-yl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under an inert atmosphere, 1.3 equivalents of mesyl chloride in 15 ml of dichloromethane are added dropwise to a solution of 0.16 mmol of the compound obtained in Step A and 2.8 equivalents of triethylamine in 1 litre of dichloromethane at 0° C. After stirring the mixture at ambient temperature for 4 days, a saturated aqueous solution of NaCl is added. After extraction, drying, filtration and concentration of the organic phase under reduced pressure, chromatography of the residue on silica gel (dichloromethane/ethanol: 97/3) enables the expected product to be isolated.

Workup

  1. extractionAfter extraction
  2. customdrying
  3. filtrationfiltration and concentration of the organic phase under reduced pressure, chromatography of the residue on silica gel (dichloromethane/ethanol: 97/3)
  4. customto be isolated

Sources & evidence

ORD record
ord-19a6dbc2aa70430ab76a3347e312fc3d
Source dataset
uspto-grants-2002_06
Patent number
US06399616B1

Reaction notes

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