Sodium borohydride → 2-Amino-3-(4-iodophenyl)propan-1-OL

HRID 76153Notes

Reaction equation

HRID 76153 reaction equation
Cl.[NH2:2][CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=1)[C:4](O)=[O:5].[BH4-].[Na+]>C(O)C.O>[NH2:2][CH:3]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([I:14])=[CH:12][CH:13]=1)[CH2:4][OH:5]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 22285256HCID 22285256, compound

Product 1

HCID 217130182-Amino-3-(4-iodophenyl)propan-1-OL

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 28.5 g (75.0 mmol) 2-amino-3-(4-iodophenyl)propanoate hydrochloride in 300 mL ethanol and 300 mL water is added to a mixture of 14.2 g (375 mmol) NaBH4 and 600 mL water (gas evolution!) and the resulting mixture is stirred at reflux for 2 h. The ethanol is evaporated in vacuo and the remaining aq. Phase is extracted with DCM (4×). The combined organic layers are dried with Na2SO4 and the solvent is removed in vacuo. The compound is used without further purification.

Workup

  1. temperatureat reflux for 2 h
  2. customThe ethanol is evaporated in vacuo
  3. extractionthe remaining aq. Phase is extracted with DCM (4×)
  4. dry with materialThe combined organic layers are dried with Na2SO4
  5. customthe solvent is removed in vacuo
  6. customThe compound is used without further purification

Sources & evidence

ORD record
ord-cc5d2484199241368fffb953ae35a58a
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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