Water → HCID 20763143, compound

HRID 219496Notes

Reaction equation

HRID 219496 reaction equation
C(O[C:6](=O)[NH:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH2:13][OH:14])(C)(C)C.O>C1COCC1>[CH3:6][NH:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH2:13][OH:14]

Participants

4

Reactant 2

HCID 962WaterHCID 592246841052648-05-1

Product 1

HCID 20763143HCID 20763143, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of [3-(2-Hydroxy-ethylamino)-propyl]-carbamic acid tert-butyl ester (900 mg, 4.1 mmol) in THF (20 mL) was added a 1M solution of BH3 in THF. The mixture was refluxed for 24 hours under nitrogen. The reaction was allowed to cool down and water (5 mL) was carefully added with vigorous stirring. The reaction mixture was concentrated to low volume and treated with a 6M aqueous solution of HCl (60 mL). The mixture was refluxed for 24 h. The mixture was concentrated to dryness then co-evaporated several time with methanol to give the desired 2-(3-methylamino-propylamino)-ethanol (399 mg, 2.46 mmol)

Workup

  1. temperatureThe mixture was refluxed for 24 hours under nitrogen
  2. temperatureto cool down
  3. concentrationThe reaction mixture was concentrated to low volume
  4. additiontreated with a 6M aqueous solution of HCl (60 mL)
  5. temperatureThe mixture was refluxed for 24 h
  6. concentrationThe mixture was concentrated to dryness

Sources & evidence

ORD record
ord-c8e44cb9376444d0b77131b8e01d1a40
Source dataset
uspto-grants-2012_06
Patent number
US08202511B2

Reaction notes

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