Tetramethyltin → HCID 9948591, compound

HRID 1682581Notes

Reaction equation

HRID 1682581 reaction equation
[CH2:1]([N:4]([CH2:23][CH2:24][CH3:25])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8](OS(C(F)(F)F)(=O)=O)[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].C[Sn](C)(C)C.[Cl-:31].[Li+].C([C:37]1C=C(C)C=C(C(C)(C)C)[C:38]=1[OH:48])(C)(C)C>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[ClH:31].[C:38]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[CH2:6][CH:5]([N:4]([CH2:23][CH2:24][CH3:25])[CH2:1][CH2:2][CH3:3])[CH2:14][CH2:13]2)(=[O:48])[CH3:37]

Participants

7

Reactant 4

HCID 11661TetramethyltinHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 433294Lithium ChlorideHCID 14973078HCID 14973078, compound

Product 1

HCID 9948591HCID 9948591, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (-)-2-(dipropylamino)-8-[(trifluromethylsulfonyl)oxyl]tetralin (910 mg, 2.4 mmol), tetramethylstannane (514 mg, 2.88 mmol), lithium chloride (315 mg, 7.44 mmol), dichloro[1,1'-bis(diphenylphosphino) ferrocene]-palladium(ii) [PdCl2 (dppf)] (12 mg, 0.144 mmol), molecular sieves (4 Å; 240 mg), 2,6-di-t-butyl-4-methylphenol (catalyst) in dimethylformamide (20 ml) was stirred under an atmosphere of carbon monoxide for 18 h at 90° C. The catalyst was filtered off and the filtrate was partitioned between water and ether. The organic layer was dried (sodium sulfate) and concentrated. The residue was chromatographed on an alumina column eluted with ether/light petroleum 1:16. Pure fractions were pooled and concentrated. The resulting oil was converted into the hydrochloride which was recrystallised from chloroform and ether to afford 323 mg (44%) of pure (-)-8-acetyl-2-(dipropylamino)tetralin hydrochloride, mp: 114°-116° C. [α]D :-123.2° C. (c 1.0, MeOH).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was partitioned between water and ether
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe residue was chromatographed on an alumina column
  6. washeluted with ether/light petroleum 1:16
  7. concentrationconcentrated
  8. customwas recrystallised from chloroform and ether

Sources & evidence

ORD record
ord-b9b7efa4d43f4084b820467ab127cdcc
Source dataset
uspto-grants-1997_06
Patent number
US05635537

Reaction notes

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