(R)-2-Amino-2-(4-fluorophenyl)ethanol → (S)-2-(5,6-Difluoro-3-nitropyridin-2-ylamino)-2-(4-fluorophenyl)ethanol

HRID 2189889Notes

Reaction equation

HRID 2189889 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[C:4](F)[N:3]=1.[NH2:13][C@H:14]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[CH2:15][OH:16]>C1COCC1>[F:8][C:7]1[CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]([NH:13][C@@H:14]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:15][OH:16])=[N:3][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 10583003(R)-2-Amino-2-(4-fluorophenyl)ethanolHCID 674554212,3,6-Trifluoro-5-nitropyridine

Product 1

HCID 67456178(S)-2-(5,6-Difluoro-3-nitropyridin-2-ylamino)-2-(4-fluorophenyl)ethanolYield 57.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,3,6-trifluoro-5-nitropyridine (1.2 g, 6.7 mmol) in THF (40 ml) was cooled to 0° C. (R)-2-amino-2-(4-fluorophenyl)ethanol (1.0 g, 6.7 mmol) was then added and the reaction was stirred at 0° C. for 30 minutes. The reaction was quenched with water (50 ml) and then extracted with DCM (2×75 ml). The combined organic fractions were dried over Na2SO4, filtered, and then concentrated. The resulting oil was purified by column chromatography (DCM-MeOH=100:1) to give the title compound (1.2 g, 57%). The product was carried over to the next step without characterization.

Workup

  1. additionwas then added
  2. customThe reaction was quenched with water (50 ml)
  3. extractionextracted with DCM (2×75 ml)
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting oil was purified by column chromatography (DCM-MeOH=100:1)

Sources & evidence

ORD record
ord-9f17b26ebf5d42bb99feabf4b18d5568
Source dataset
uspto-grants-2012_12
Patent number
US08324252B2

Reaction notes

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