Borane → 5-(2-Benzyloxy-4-cyclopentylmethylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

HRID 660776

Reaktionsgleichung

Reaktionsgleichung von HRID 660776
[CH2:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.B1C2CCCC1CCC2.[CH2:16]([O:23][C:24]1[CH:29]=[C:28](I)[CH:27]=[CH:26][C:25]=1[N:31]1[S:35](=[O:37])(=[O:36])[NH:34][C:33](=[O:38])[CH2:32]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.B.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.COCCOC>[CH2:16]([O:23][C:24]1[CH:29]=[C:28]([CH2:1][CH:2]2[CH2:6][CH2:5][CH2:4][CH2:3]2)[CH:27]=[CH:26][C:25]=1[N:31]1[S:35](=[O:37])(=[O:36])[NH:34][C:33](=[O:38])[CH2:32]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

8

Edukt 5

HCID 6331BoraneHCID 10340Sodium CarbonateHCID 73714Cyclopentane, methylene-HCID 789669-Borabicyclo(3.3.1)nonaneHCID 688386435-(2-Benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Produkt 1

HCID 688388965-(2-Benzyloxy-4-cyclopentylmethylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a solution of methylenecyclopentane (246 mg, 3 mmol) in THF (7.5 mL) is added 9-BBN (7.5 mL, 0.5M in THF, 3 mmol) and the mixture is stirred at RT for 18 h. A mixture of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (200 mg, 0.45 mmol), 3.38 mL of the borane solution previously prepared (0.675 mmol), resin-bound PPh3Pd (100 mg) and Na2CO3 (0.9 mL, 2M) in DME (5 mL) is heated in a microwave apparatus at 110° C. for 15 min. The mixture is filtered and the solvent removed under reduced pressure to give the title compound which is used directly in the next step.

Aufarbeitung

  1. temperatureis heated in a microwave apparatus at 110° C. for 15 min
  2. filtrationThe mixture is filtered
  3. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-78aa73b023354cb0974bc10b0523b56f
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084448B2

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