(S)-2-(Trifluoromethyl)-3-(benzylamino)propane-1,2-diol → 1,2-Propanediol, 2-(aminomethyl)-3,3,3-trifluoro-, (2S)-
Reaction equation
[F:1][C:2]([F:17])([F:16])[C@@:3]([CH2:7][NH:8]CC1C=CC=CC=1)([OH:6])[CH2:4][OH:5].[H][H]>CO.[Pd]>[NH2:8][CH2:7][C@@:3]([OH:6])([C:2]([F:17])([F:16])[F:1])[CH2:4][OH:5]Participants
5
Procedure
(S)-3,3,3-Trifluoro-2-{[(phenylmethyl)amino]methyl}-1,2-propanediol (160 mg) was dissolved in methanol (1.5 ml) and hydrogenated using 10% palladium on carbon as the catalyst and the H-cube (Thales) as the hydrogen source. The solvent was carefully evaporated to give a pinkish volatile oil (112 mg) which by 1H NMR still contained 13% starting material. Therefore this was re-dissolved in methanol (2 ml) and re-hydrogenated using the H-cube. The solvent was evaporated to give the title compound as a pink/brown oil (93 mg).
Workup
- customThe solvent was carefully evaporated
Sources & evidence
- ORD record
- ord-bbe503b585a74c9e892b0738621e6d6f
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247377B2
Reaction notes
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