Hydrochloric Acid → HCID 58856349, compound

HRID 899465Notes

Reaction equation

HRID 899465 reaction equation
[NH2:1][C:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH2:6][F:7])[C:3](O)=[O:4].B.O1CCCC1.Cl>C1COCC1>[NH2:1][C:2]([CH2:6][F:7])([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][OH:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 67318972HCID 67318972, compound

Product 1

HCID 58856349HCID 58856349, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-amino-2-benzyl-3-fluoropropanoic acid (50 mg, 0.25 mmol) (for synthesis see EP 0 040 150 A1) in 2.5 mL THF, cooled to 0° C., was added borane-tetrahydrofuran complex (1M in THF, 0.75 mL, 0.75 mmol) dropwise. The reaction was stirred at rt overnight, quenched with MeOH and concentrated. Hydrochloric acid (1M, 7.5 mL, 7.5 mmol) was added, the mixture was heated to 45° C. for 1 h and concentrated. The reaction was made basic with saturated NaHCO3 and exacted with CHCl3. Drying and solvent evaporation gave 2-amino-2-(fluoromethyl)-3-phenylpropan-1-ol. 1H NMR (400 MHz, CDCl3) δ 7.35-7.21 (m, 5H), 4.30-4.11 (two q, ABX system, J=47.4 Hz, J=20.8 Hz, J=9.0 Hz, 2H), 3.49 (m, 2H), 2.76 (m, 2H).

Workup

  1. customquenched with MeOH
  2. concentrationconcentrated
  3. temperaturethe mixture was heated to 45° C. for 1 h
  4. concentrationconcentrated
  5. customDrying
  6. customsolvent evaporation

Sources & evidence

ORD record
ord-f23e6449b63544ebbe95effb4677910a
Source dataset
uspto-grants-2008_04
Patent number
US07354942B2

Reaction notes

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