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

HRID 660776

Reaction equation

HRID 660776 reaction equation
[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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-78aa73b023354cb0974bc10b0523b56f
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Linked notes

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