Acetone → (4S,5R)-4-(fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidine

Reaction equation

[NH2:1][C@H:2]([CH2:12][F:13])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1)[OH:4].[CH3:14][C:15]([CH3:17])=O>>[F:13][CH2:12][C@@H:2]1[C@@H:3]([C:5]2[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=2)[O:4][C:15]([CH3:17])([CH3:14])[NH:1]1

Participants

Reactant 2

HCID 180Acetone

HCID 45257860(2S,1R)-2-Amino-3-fluoro-1-(4-iodo-phenyl)-propan-1-ol

Product 1

HCID 86695412(4S,5R)-4-(fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidine

Procedure

Acetone (150 mL) is added to commercially available (1R,2S)-2-amino-3-fluoro-1-(4-iodophenyl)propan-1-ol (15.0 g, 50.8 mmol). After stirring overnight at room temperature the solvent is removed under reduced pressure to give the title compound (17.6 g): m/z (Cl) M+H 335.

Workup

customis removed under reduced pressure

Sources & evidence

ORD record: ord-4080bd6bd812480387b66880a266b59b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340564B2

Reaction notes

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