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

HRID 660776

반응식

HRID 660776 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-78aa73b023354cb0974bc10b0523b56f
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084448B2

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