Diethanolamine → (S)-3-(2-Chlorophenyl)-1-(3-(2-(6,7-difluoro-2-quinolinyl)ethenyl)phenyl) propanol

HRID 1755777Notes

Reaction equation

HRID 1755777 reaction equation
B(Cl)([C@H]1[C@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1)[C@H]1[C@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][CH2:31][C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH:40]=[CH:41][C:42]2[CH:51]=[CH:50][C:49]3[C:44](=[CH:45][C:46]([F:53])=[C:47]([F:52])[CH:48]=3)[N:43]=2)[CH:35]=1)=[O:33].N(CCO)CCO>C(Cl)Cl>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][CH2:31][C@@H:32]([C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH:40]=[CH:41][C:42]2[CH:51]=[CH:50][C:49]3[C:44](=[CH:45][C:46]([F:53])=[C:47]([F:52])[CH:48]=3)[N:43]=2)[CH:35]=1)[OH:33]

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 11131038Chlorobis((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)boraneHCID 537280503-(2-Chlorophenyl)-1-(3-(2-(6,7-difluoro-2-quinolinyl)ethenyl)phenyl)-1-propanone

Product 1

HCID 54456899(S)-3-(2-Chlorophenyl)-1-(3-(2-(6,7-difluoro-2-quinolinyl)ethenyl)phenyl) propanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

At -20° C., a solution of (-)-B-chlorodiisopinocampheylborane (1.74 g, 1.5 equiv.) in 9 mL of CH2Cl2 was added dropwise to a suspension of the ketone of Step 4 (1.52 g, 3.5 mmol) in 18 mL of CH2Cl2 and the mixture was stirred at 0° C. for an hour and at room temperature for 2 hours. At 0° C., 10% aq. diethanolamine was added and the mixture was stirred at r.t. for 30 min. The product was extracted in EtOAc:THF 1:1, washed with brine, dried over Na2SO4, and concentrated. The oil was dissolved in ether and conc. HCl (5 ml) was added. The precipitated hydrochloride was filtered, washed with ether, and dissolved in THF:0.1 N NaOH. The product was extracted in EtOAc:THF 1:1, washed with brine, dried over Na2SO4 and purified by flash chromatography with EtOAc:toluene 10:90. Yield 1.125 g, 74%.

Workup

  1. stirringthe mixture was stirred at r.t. for 30 min
  2. extractionThe product was extracted in EtOAc:THF 1:1
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. dissolutionThe oil was dissolved in ether
  7. additionconc. HCl (5 ml) was added
  8. filtrationThe precipitated hydrochloride was filtered
  9. washwashed with ether
  10. dissolutiondissolved in THF
  11. extractionThe product was extracted in EtOAc:THF 1:1
  12. washwashed with brine
  13. dry with materialdried over Na2SO4
  14. custompurified by flash chromatography with EtOAc:toluene 10:90

Sources & evidence

ORD record
ord-4dc5bd8b23d54072b113804ec2691528
Source dataset
uspto-grants-1995_08
Patent number
US05438141

Reaction notes

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