Stannous chloride dihydrate → HCID 66932414, compound

HRID 518219Notes

Reaction equation

HRID 518219 reaction equation
[CH3:1][O:2][C:3](=[O:33])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:29](=[CH:30][CH:31]=1)[O:28][C:11]1([CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=3)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:32].O.O.Cl[Sn]Cl.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].C(=O)(O)[O-].[Na+]>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:33])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:29](=[CH:30][CH:31]=1)[O:28][C:11]1([CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=3)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:32]

Participants

6

Reactant 4

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 9855836Potassium sodium tartarateHCID 66932419HCID 66932419, compound

Product 1

HCID 66932414HCID 66932414, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(E)-3-{1′-[2-(4-Nitro-phenyl-)ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (377 mg, 0.833 mmol) was dissolved in AcOEt. SnCl2.2H2O (753 mg, 3.35 mmol) was added and the mixture heated under reflux for 12 h. After cooling down to room temperature the solution was treated with an aqueous solution of sodium potassium tartrate and sodium bicarbonate, and the organic phase was separated, dried and evaporated. The crude product was purified by column chromatography (eluent: DCM/MeOH 99:1 to 97:3) to give (E)-3-{1′-[2-(4-amino-phenyl)-ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid methyl ester (225 mg) as a light brown solid.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 12 h
  3. customthe organic phase was separated
  4. customdried
  5. customevaporated
  6. customThe crude product was purified by column chromatography (eluent: DCM/MeOH 99:1 to 97:3)

Sources & evidence

ORD record
ord-9736c0a178664276913b467138f99ed7
Source dataset
uspto-grants-2015_08
Patent number
US09115148B2

Reaction notes

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