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

HRID 75929Notes

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

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

Workup

additionwas then added
customThe reaction was quenched with water (50 ml)
extractionextracted with DCM (2×75 ml)
customThe combined organic fractions were dried over

Sources & evidence

ORD record: ord-bf037e367d3a4158bb01bd508beaee61
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835465B2

Reaction notes

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