Ammonia → Methyl 4,4,4-trifluoro-3-oxobutanoate

HRID 1111069Notes

Reaction equation

HRID 1111069 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1(O)[CH:8]([C:9]([O:11][CH3:12])=[O:10])[CH:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH:6]([C:17]([O:19][CH3:20])=[O:18])[C:5]([C:22]([F:25])([F:24])[F:23])([OH:21])[O:4]1.[NH3:29]>O1CCCC1>[F:1][C:2]([F:27])([F:28])[C:3](=[O:4])[CH2:8][C:9]([O:11][CH3:12])=[O:10].[F:1][C:2]([F:28])([F:27])[C:3]1([OH:4])[CH:8]([C:9]([O:11][CH3:12])=[O:10])[CH:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH:6]([C:17]([O:19][CH3:20])=[O:18])[C:5]([C:22]([F:25])([F:24])[F:23])([OH:21])[NH:29]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 13745974Dimethyl 2,6-bis(trifluoromethyl)-2,6-dihydroxy-4-isobutyl-tetrahydro-3,5-pyrandicarboxylate

Product 2

HCID 550266Methyl 4,4,4-trifluoro-3-oxobutanoateHCID 13745991Dimethyl 2,6-bis(trifluoromethyl)-2,6-dihydroxy-4-isobutyl-3,5-piperidinedicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 344 g (0.920 mole) crude product from Example b in 500 ml of tetrahydrofuran (THF) is passed 58 g (3.41 mole) of gaseous ammonia for 3 hours. The reaction mixture is concentrated and the residue (332 g) is recrystallized from hexaneether to give 53.7 g (13% yield from methyl trifluoroacetoacetate) of the desired product as a white solid, m.p. 102°-106° C.

Workup

  1. customfor 3 hours
  2. concentrationThe reaction mixture is concentrated
  3. customthe residue (332 g) is recrystallized from hexaneether

Sources & evidence

ORD record
ord-6d330343c00c43a08dd4836d024545a7
Source dataset
uspto-grants-1990_12
Patent number
US04978384

Reaction notes

Loading…