Iodine → HCID 11623636, compound

HRID 1676901Notes

Reaction equation

HRID 1676901 reaction equation
[NH2:1][C:2]1([C:21](O)=[O:22])[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=2)[CH2:3]1.[BH4-].[Na+].II>C1COCC1>[NH2:1][C:2]1([CH2:21][OH:22])[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:11][CH:12]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 807IodineHCID 4311764Sodium borohydrideHCID 57443797HCID 57443797, compound

Product 1

HCID 11623636HCID 11623636, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

63.4 mg (0.2 mmol) of 5 and 27 mg (0.6 mmol) sodium borohydride were dissolved in 3 mL of THF. After the solution was cooled to 0° C., 51 mg (0.2 mmol) I2 was dissolved in 1 mL THF and added dropwise. Then the vessel was fitted with a condenser and the reaction mixture was refluxed under N2 for 5 hrs. Excess NaBH4 was quenched with methanol. After removal of solvent, 2 mL water and 5 mL methylene chloride was added, the mixture was stirred for about 1 hr until the organic layer became clear. The organic phase was collected and aqueous phase was further extracted twice with methylene chloride. The combined organic extraction was dried and concentrated to provide 43 mg (71%) of the crude product. Further purification on TLC with methanol/chloroform (5:95) provided 13 mg of clear oil. J. Org. Chem., 1993, 58, 3568-3571. 1H NMR (CD3OD) δ 7.11 (m, 4H, ArH), 3.80 (t, J=7.5 Hz, 1H, c-pentyl-CH2O), 3.67 (t, J=7.5 Hz, 1H, c-pentyl-CH2O), 3.01 (m, 1H, ArCHCC), 2.55 (t, J=7.5 Hz, 2H, ArCH2), 2.29-1.69 (m, 6H, cyclo-pentyl), 1.57 (m, 2H, ArCH2CH2), 1.38-1.28 (m, 10H, CH2), 0.89 (t, J=7.5 Hz, 3H, CH3); 13C NMR (CD3COCD3) δ 141, 128, 127, 96, 45, 44, 43, 35, 35, 33, 33, 32, 32, 29, 29, 29, 23, 13.

Workup

  1. additionadded dropwise
  2. customThen the vessel was fitted with a condenser
  3. temperaturethe reaction mixture was refluxed under N2 for 5 hrs
  4. customExcess NaBH4 was quenched with methanol
  5. customAfter removal of solvent, 2 mL water and 5 mL methylene chloride
  6. additionwas added
  7. customThe organic phase was collected
  8. extractionaqueous phase was further extracted twice with methylene chloride
  9. extractionThe combined organic extraction
  10. customwas dried
  11. concentrationconcentrated
  12. customto provide 43 mg (71%) of the crude product
  13. customFurther purification on TLC with methanol/chloroform (5:95)

Sources & evidence

ORD record
ord-bb92ab95bca5495c8e54abfb21d6f620
Source dataset
uspto-grants-2011_08
Patent number
US08008286B2

Reaction notes

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