Sodium Iodide → HCID 67187886, compound

HRID 549652Notes

Reaction equation

HRID 549652 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[CH2:10][CH2:11][C:12](=[CH2:25])[CH2:13][CH2:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1.CC([O-])=O.[Na+].[Na+].[I-:39].CC1C=CC(S(NCl)(=O)=O)=CC=1>C1COCC1>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][CH2:13][CH:12]([CH2:25][I:39])[CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 31388TosylchloramideHCID 517045Sodium AcetateHCID 2723981Borane;tetrahydrofuranHCID 67191800Dibenzyl-4-methyleneheptanedioate

Product 1

HCID 67187886HCID 67187886, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound B4 (176 mg, 0.5 mmol) was dissolved in anhydrous THF (0.5 mL). The solution was cooled to 0° C. and BH3-THF (2.0 M, 0.25 mL, 0.5 mmol) was added via a syringe. The solution was then stirred at room temperature for 1 h. Methanolic NaOAc (3.0 mL, 1.0 M, 3.0 mmol), aqueous NaI (3.0 mL, 1.0 M, 3.0 mmol) and methanolic chloramine-T (6.0 mL, 0.5 M, 3.0 mmol) were added sequentially to the organoborane solution at room temperature. The reaction mixture were stirred for 10 min at room temperature and then quenched with aqueous Na2S2O3 (1.0 M). The mixture was partitioned between Et2O (50 mL) and H2O (50 mL) and the organic layer was washed with brine (30 mL) before drying over Na2SO4. The solvent was evaporated and the residue was subjected to silica chromatography (CH2Cl2/hexanes, 2/100 to 7/100) to yield compound 1b (85 mg). The yield was 35%. 1H NMR (200 MHz, CDCl3) δ 7.37 (m, 10H), 5.11 (s, 4H), 3.21 (d, 2H, J=8.0 Hz), 2.37 (m, 4H), 1.68 (m, 4H), 1.20 (m, 1H); 13C NMR (50 MHz, CDCl3) δ 173.2, 136.3, 129.1, 128.8, 66.9, 37.5, 31.8, 29.9, 14.5; MS (MALDI-TOF) calcd (M+Na+) 503.3, found 503.8.

Workup

  1. stirringThe reaction mixture were stirred for 10 min at room temperature
  2. customquenched with aqueous Na2S2O3 (1.0 M)
  3. customThe mixture was partitioned between Et2O (50 mL) and H2O (50 mL)
  4. washthe organic layer was washed with brine (30 mL)
  5. dry with materialbefore drying over Na2SO4
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-f72a93c7a98741c28e95c30a3300f034
Source dataset
uspto-grants-2011_05
Patent number
US07943751B2

Reaction notes

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