Hydrochloric Acid → (S)-3-amino-3-(5-bromo-2-fluorophenyl)-4,4-difluorobutan-1-ol

HRID 876371Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6]([C@@:8]([NH:15][S@](C(C)(C)C)=O)([CH2:12][CH2:13][OH:14])[CH:9]([F:11])[F:10])[CH:7]=1.Cl.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[NH2:15][C@@:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:22])([CH:9]([F:10])[F:11])[CH2:12][CH2:13][OH:14]

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of (S)—N—((S)-2-(5-bromo-2-fluorophenyl)-1,1-difluoro-4-hydroxybutan-2-yl)-2-methylpropane-2-sulfinamide (intermediate E4.1) (810 mg, 2.01 mmol) in THF (40 ml) was added conc. HCl (595 mg, 496 μl, 6.04 mmol) at 23° C. The mixture was stirred for 4 hours at 23° C. Poured into 1 M Na2CO3-solution, extracted with ethyl acetate and dried over Na2SO4. Removal of solvent in vacuum left (S)-3-amino-3-(5-bromo-2-fluorophenyl)-4,4-difluorobutan-1-ol (570 mg, 1.91 mmol, 95.0% yield) as a light yellow oil. The crude product was used in the next step without further purification. MS (ISP): m/z=298.1 [M+H]+ and 300.1 [M+2+H]+.

Workup

extractionextracted with ethyl acetate
dry with materialdried over Na2SO4
customRemoval of solvent in vacuum

Sources & evidence

ORD record: ord-4db6798b3f9447ffb0ea8ffa256a474f
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987255B2

Reaction notes

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