(2S)-2-amino-4-fluoro-4-methylpentan-1-ol → (4S)-4-(2-Fluoro-2-methylpropyl)-2-oxazolidinone

HRID 2246766Notes

Reaction equation

HRID 2246766 reaction equation
[F:1][C:2]([CH3:9])([CH3:8])[CH2:3][C@@H:4]([CH2:6][OH:7])[NH2:5].CC(=C)C[C@H]1C[O:16][C:15](=O)N1>N1C=CC=CC=1>[F:1][C:2]([CH3:9])([CH3:8])[CH2:3][C@H:4]1[CH2:6][O:7][C:15](=[O:16])[NH:5]1

Participants

4

Reactant 2

HCID 12167160(2S)-2-amino-4-fluoro-4-methylpentan-1-olHCID 57463978(4S)-4-(2-methylprop-2-enyl)-1,3-oxazolidin-2-one

Product 1

HCID 11194496(4S)-4-(2-Fluoro-2-methylpropyl)-2-oxazolidinone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The 4-fluoroleucinol may be synthesized according to Scheme 5. 4,5-Dehydroleucine is converted to (4S)-4-(2-methylprop-2-enyl)-1,3-oxazolidin-2-one as described in the scheme below. This intermediate is then treated with a hydrofluorination reagent such as BF-pyridine to give (4S)-4-(2-fluoro-2-methylpropyl)-1,3-oxazolidin-2-one. Basic hydrolysis (i.e. Ba(OH)2 or NaOH) then affords (2S)-2-amino-4-fluoro-4-methylpentan-1-ol, which may be used as shown in Scheme 2. Selective protection of the alcohol provides an intermediate that can be used in Scheme 3.

Sources & evidence

ORD record
ord-7f13b1d42093481a8bc2dca03331a87b
Source dataset
uspto-grants-2010_03
Patent number
US07687524B2

Reaction notes

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