Butyric Acid → HCID 2779071, compound

HRID 861813Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[CH:3]([OH:10])[CH2:4][C:5]([O:7]CC)=[O:6].[Na].C(O)(=O)CCC.C[C@H](N)C1C=CC=CC=1>>[F:1][C:2]([F:12])([F:11])[C@H:3]([OH:10])[CH2:4][C:5]([OH:7])=[O:6]

Participants

Reactant 4

HCID 264Butyric Acid

HCID 758181-Phenethylamine, (-)-

HCID 136210Ethyl 4,4,4-trifluoro-3-hydroxybutanoate

HCID 5360545Sodium

Product 1

HCID 2779071HCID 2779071, compound

Procedure

According to this process, ethyl (±)-4,4,4-trifluoro-3-hydroxybutanoate is converted to the sodium salt of the corresponding butanoic acid which is hydrolysed to give (±)-4,4,4-trifluoro-3-hydroxbutanoic acid, this acid is reacted with (S)-α-methylbenzylamine, the (S)-α-methylbenzylamine salt of 4,4,4-trifluoro-3(R)-hydroxybutanoic acid is separated from the mixture of diastereoisomers formed by crystallization from ethanol and this salt is then hydrolysed in acid medium to produce 4,4,4-trifluoro-3(R)-hydroxybutanoic acid. 4,4,4-Trifluoro-1,3(R)-butanediol is then obtained by reduction of 4,4,4-trifluoro-3(R)-hydroxybutanoic acid.

Workup

customto give (±)-4,4,4-trifluoro-3-hydroxbutanoic acid
customthe (S)-α-methylbenzylamine salt of 4,4,4-trifluoro-3(R)-hydroxybutanoic acid is separated from the mixture of diastereoisomers
customformed by crystallization from ethanol

Sources & evidence

ORD record: ord-939de3731e794b5eb56697e4f7b2dd6b
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05716841

Reaction notes

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