Dibutyltin dichloride → HCID 57795442, compound

HRID 2099610Notes

Reaction equation

HRID 2099610 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH2:10])=[O:4].[CH2:11]1[O:21][C:14]2([CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]2)[O:13][CH2:12]1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][CH:17]1[CH2:18][CH2:19][C:14]2([O:21][CH2:11][CH2:12][O:13]2)[CH2:15][CH2:16]1)=[O:4]

Participants

6

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 57795442HCID 57795442, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 3-amino-thiophene-2-carboxylic acid methyl ester (5.0 g, 31.85 mmol) in dry THF (9 mL) was treated with 1,4-cyclohexanedione monoethylene ketal (5.0 g, 32.05 mmol), followed by dibutyltin dichloride (482 mg, 1.59 mmol). After 5 min, phenyl silane (4.3 mL, 34.96 mmol) was added and the reaction mixture was stirred overnight at room temperature. After concentration, the residue was dissolved in EtOAc and washed with NaHCO3 followed by brine. The organic layer was separated, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using 30% ethyl acetate in hexane as eluent to give 3-(1,4-dioxa-spiro[4.5]dec-8-ylamino)-thiophene-2-carboxylic acid methyl ester (4.5 g, 47% yield).

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with NaHCO3
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f111413089834254a20b67a196cb6b4a
Source dataset
uspto-grants-2009_08
Patent number
US07569600B2

Reaction notes

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