Boron trifluoride etherate → 2-Amino-2-(3-bromophenyl)propan-1-ol

HRID 221661Notes

Reaction equation

HRID 221661 reaction equation
[BH4-].[Na+].Cl.[NH2:4][C:5]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[CH:11]=1)([CH3:9])[C:6](O)=[O:7].B(F)(F)F.O(CC)CC>C1COCC1>[NH2:4][C:5]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[CH:11]=1)([CH3:9])[CH2:6][OH:7]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 223369922-Amino-2-(3-bromophenyl)propanoic acid hydrochloride

Product 1

HCID 532566942-Amino-2-(3-bromophenyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaBH4 (38 g, 1.125 mol) was added at room temperature to a slurry of 2-amino-2-(3-bromo-phenyl)-propionic acid hydrochloride (105 g, 375 mmol) in dry THF. At 0° C. BF3—O(C2H5)2 (158 g, 1.125 mol) was added dropwise. The mixture was allowed to warm to room temperature, stirred for three days, quenched with 1M aqueous NaOH solution, concentrated in vacuo to remove the THF and extracted with EtOAc (3×300 ml). The organic phase was washed with 1M aqueous NaOH solution, dried with sodium sulfate and concentrated in vacuo to yield the title compound, which was used in the next reaction step without further purification. 1H-NMR (400 MHz, CDCl3): 7.61 (s, 1H), 7.35 (m, 2H), 7.21 (m, 1H), 3.58 (q, 2H), 1.42 (s, 3H).

Workup

  1. customAt 0° C
  2. customquenched with 1M aqueous NaOH solution
  3. concentrationconcentrated in vacuo
  4. customto remove the THF
  5. extractionextracted with EtOAc (3×300 ml)
  6. washThe organic phase was washed with 1M aqueous NaOH solution
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0df768d7e53640f9b21c16192d2bff78
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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