Sodium Carbonate → HCID 25257234, compound

HRID 2078444Notes

Reaction equation

HRID 2078444 reaction equation
[F:1][C:2]([F:34])([O:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:33])([F:32])[F:31])[CH:24]=3)[N:14]=2)[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4].[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.CCOC(C1CC(C(OCC)=O)=C(C)NC=1C)=O.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.C1(C)C=CC=CC=1>[F:34][C:2]([F:1])([O:6][C:7]1[CH:8]=[C:9]([C@H:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:31])([F:32])[F:33])[CH:24]=3)[NH:14]2)[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 70849Hantzsch esterHCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 50900130HCID 50900130, compound

Product 1

HCID 25257234HCID 25257234, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
58 °C

Procedure

(also known as 4-oxo-2,6-di-phenanthren-9-yl-3,5-dioxa-4l5-phospha-cyclohepta[2,1-a; 3,4-a′]dinaphthalen-4-ol) (44.5 mg, 0.06 mmoL, 3 mol %), was added a solution made from 2-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)-5-(3-(trifluoromethoxy)phenyl)quinoline (1.02 g, 2.12 mmoL) and toluene (3.61 g). The resulting slurry was stirred, heated to 58° C. and then stirred at 58° C. for 8 hours. The resulting mixture was then cooled to room temperature. (1S)-(+)-10-camphorsulfonic acid (148 mg, 0.30 eq) and additional diludine (160 mg, 0.3 eq.) were added and the resulting slurry was stirred at room temperature for 6 hours. To the resulting reaction mixture were added ethyl acetate (4 mL) and aqueous 2N Na2CO3 (6 mL). The phases of the resulting biphasic mixture wre separated. After the clear lower aqueous layer was mostly removed, the remaining organic phase and some precipitates were filtered and the filtrate was washed with 4N HCl for (3-5 times, 6 mL each time), followed by washing with 50% saturated aqueous Na2CO3 solution (2×). The resulting mixture was concentrated to yield the title compound, (R)-2-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)-5-(3-(trifluoromethoxy)phenyl)-1,2,3,4-tetrahydroquinoline, as crude product, as an oil.

Workup

  1. additionwas added a solution
  2. stirringstirred at 58° C. for 8 hours
  3. temperatureThe resulting mixture was then cooled to room temperature
  4. stirringthe resulting slurry was stirred at room temperature for 6 hours
  5. customTo the resulting reaction mixture
  6. customThe phases of the resulting biphasic mixture wre separated
  7. customAfter the clear lower aqueous layer was mostly removed
  8. filtrationthe remaining organic phase and some precipitates were filtered
  9. washthe filtrate was washed with 4N HCl for (3-5 times, 6 mL each time)
  10. washby washing with 50% saturated aqueous Na2CO3 solution (2×)
  11. concentrationThe resulting mixture was concentrated

Sources & evidence

ORD record
ord-0e5d8dde325946e0b35bc05cdc6b7385
Source dataset
uspto-grants-2011_04
Patent number
US07928238B2

Reaction notes

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