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

HRID 1018985Notes

Reaction equation

HRID 1018985 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-0fc30f5eb56a4be7875caa7ca78b2758
Source dataset
uspto-grants-2002_11
Patent number
US06486171B2

Reaction notes

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