1-Phenethylamine, (-)- → (2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid

HRID 1814809Notes

Reaction equation

HRID 1814809 reaction equation
[OH:1][C:2]([CH3:10])([C:6]([F:9])([F:8])[F:7])[C:3]([OH:5])=[O:4].C1([C@@H](N)C)C=CC=CC=1>CO>[OH:1][C@@:2]([CH3:10])([C:6]([F:9])([F:8])[F:7])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid

Product 1

HCID 2760712(2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R/S)-2-Hydroxy-2-methyl-3,3,3-trifluoropropanoic acid was resolved according to the resolution method described in European Patent Application No. EP 524781 (described for the preparation of the (S)-(−)-acid) except that (1S,2R)-norephedrine was used in place of (1R,2S)-norephedrine or (S)-(−)-1-phenylethylamine to yield the title compound, [α]D20 +18.1° C. (c, 8.8 in MeOH); NMR analysis of the acid in the presence of (R)-(+)-1-phenylethylaine gave an enantiomerical purity of >98%. NMR (CDCl3): 1.27 (s, 3H) for the (R)-enantiomer, 1.21 (s, 3H) for the (S)-enantiomer.

Sources & evidence

ORD record
ord-c5a1e936bfc146a6b293d65bb848315b
Source dataset
uspto-grants-2005_04
Patent number
US06878712B1

Reaction notes

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