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

HRID 660776

反応式

HRID 660776 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-78aa73b023354cb0974bc10b0523b56f
出典データセット
uspto-grants-2011_12
特許番号
US08084448B2

関連ノート

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