Trifluoroacetic acid → HCID 21480573, compound

HRID 1490168Notes

Reaction equation

HRID 1490168 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:12][C:11]2[CH2:10][CH:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH2:8][CH2:7][C:6]=2[NH:5][C:4]1=[O:22].C(O)(C(F)(F)F)=O>C([SiH](CC)CC)C>[OH:1][CH2:2][CH:3]1[CH2:12][CH:11]2[CH:6]([CH2:7][CH2:8][CH:9]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[CH2:10]2)[NH:5][C:4]1=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18967712HCID 18967712, compound

Product 1

HCID 21480573HCID 21480573, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 12052TriethylsilaneSolvent

Procedure

3,4,5,6,7,8-Hexahydro-3-hydroxymethyl-6-((4-methoxyphenyl)methyl)quinolin-2[1H]-one (6.75 g) (prepared according to Example 17) was suspended in triethylsilane (35 ml) and TFA (17.25) ml was added with rapid stirring. When tlc (SiO2 /EtOAc) showed no starting material remained, the stirring was stopped and the reaction mixture separated into two layers. The lower (TFA) layer was added to a saturated solution of sodium carbonate and this organic solution was extracted into dichloromethane, dried (MgSO4) and evaporated. The residue (9.4 g) was purified in several fractions to give 3,4,4a,5,6,7,8,8a-octahydro-3-hydroxymethyl-6-((4-methoxyphenyl)methyl)quinolin-2[1H]-one (mixed isomers 4.58 g). This product was purified by chromatography on a "Dynamax" 60A Si 21×250 mm column using 0.25% NH4OH, 1.8% MeOH in dichloromethane as mobile phase. A flow rate of 21.6 ml/min was used and injections of 10 ml of 10 mg/ml of product in mobile phase were made. The material eluting at 20.1 minutes was collected and recrystallised from ethyl acetate to give the title compound (0.2 g) mp 196°-197° C.

Workup

  1. customthe reaction mixture separated into two layers
  2. additionThe lower (TFA) layer was added to a saturated solution of sodium carbonate
  3. extractionthis organic solution was extracted into dichloromethane
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue (9.4 g) was purified in several fractions

Sources & evidence

ORD record
ord-03e7add2500646e9b0f688061844d059
Source dataset
uspto-grants-1997_10
Patent number
US05681839

Reaction notes

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