Iodine → HCID 57495610, compound

HRID 1092341Notes

Reaction equation

HRID 1092341 reaction equation
[BH4-].[Na+].[CH:3]1([CH:6]([NH:10][CH:11]2[CH2:13][CH2:12]2)[C:7](O)=[O:8])[CH2:5][CH2:4]1.II.[H][H]>C1COCC1>[CH:3]1([CH:6]([NH:10][CH:11]2[CH2:13][CH2:12]2)[CH2:7][OH:8])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 807IodineHCID 4311764Sodium borohydrideHCID 57495609HCID 57495609, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 57495610HCID 57495610, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (200 mg) was added to THF (10 mL), followed by cyclopropyl-cyclopropylamino-acetic acid (1 g of the material obtained in step B]). The mixture was cooled to 0° C. and a solution of iodine (558 mg) in THF (5 mL) was added carefully drop by drop over a period of 30 minutes. Vigorous hydrogen evolution was observed. The mixture was stirred at 0° C. for 30 minutes and then heated to reflux for 2 hours. The mixture was cooled and quenched with methanol until a clear solution was obtained. The solution was stirred for 30 minutes and then evaporated in vacuo. The residue was treated with 20% KOH (10 mL) and extracted with DCM. The combined organic extracts were dried over Na2SO4 and evaporated. The crude material was purified by flash chromatography using methanol/ethyl acetate 2:3 as an eluent to give 2-cyclopropyl-2-cyclopropylamino-ethanol (73 mg) as a colorless oil. MS (ESI): 142.2 (MH+).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. temperatureThe mixture was cooled
  4. customquenched with methanol until a clear solution
  5. customwas obtained
  6. stirringThe solution was stirred for 30 minutes
  7. customevaporated in vacuo
  8. additionThe residue was treated with 20% KOH (10 mL)
  9. extractionextracted with DCM
  10. dry with materialThe combined organic extracts were dried over Na2SO4
  11. customevaporated
  12. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-2dca8c06dc4f4a2f9199e562820e2f58
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

Loading…