Borane;tetrahydrofuran → Methyl 2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3(R)-hydroxypropyl)benzoate

HRID 249041Notes

Reaction equation

HRID 249041 reaction equation
O1C=CB=N1.[Cl:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([CH:17]=[CH:18][C:19]3[CH:20]=[C:21]([C:25](=[O:38])[CH2:26][CH2:27][C:28]4[CH:37]=[CH:36][CH:35]=[CH:34][C:29]=4[C:30]([O:32][CH3:33])=[O:31])[CH:22]=[CH:23][CH:24]=3)=[N:14]2)=[CH:9][CH:8]=1.B.C1COCC1>C1COCC1>[Cl:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([CH:17]=[CH:18][C:19]3[CH:20]=[C:21]([C@H:25]([OH:38])[CH2:26][CH2:27][C:28]4[CH:37]=[CH:36][CH:35]=[CH:34][C:29]=4[C:30]([O:32][CH3:33])=[O:31])[CH:22]=[CH:23][CH:24]=3)=[N:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 2723981Borane;tetrahydrofuranHCID 53394881Methyl 2-(3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-oxopropyl)benzoateHCID 57082634Oxazaborole

Product 1

HCID 54006302Methyl 2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3(R)-hydroxypropyl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

At -20° C., a solution of (S)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo(1,2-c) (1,3,2,) oxazaborole.borane complex (J. Am. Chem. Soc., 104, 5551-5553 (1987) 6.34 g, 21.8 mmol) in anhydrous THF (20 ml) was added dropwise to a solution of the ketone of Step 2 (33.1 g, 72.6 mmol) in THF (300 mL). Then, 1.0M BH3.THF (108 ml) was added slowly and the reaction mixture was slowly warmed up to -5° C. within 3-4 hours. The mixture was added to an ice cold 25% NH4OAc solution. The product was extracted into hot EtOAc, dried over Na2So4, concentrated to dryness and co-evaporated twice with toluene. It was dissolved in hot toluene and filtered through silica (~400 ml) with toluene and EtOAc:toluene 10:90 and 15:85. The product was finally recrystallized as a hydrate from toluene containing 4 mL H2O. [α ]D : +29.5° (c=1.82, CHCl3).

Workup

  1. customAt -20° C.
  2. extractionThe product was extracted into hot EtOAc
  3. customdried over Na2So4
  4. concentrationconcentrated to dryness
  5. dissolutionIt was dissolved in hot toluene
  6. filtrationfiltered through silica (~400 ml) with toluene and EtOAc:toluene 10:90 and 15:85
  7. customThe product was finally recrystallized as a hydrate from toluene containing 4 mL H2O
  8. custom+29.5° (c=1.82, CHCl3)

Sources & evidence

ORD record
ord-a8a2fd0d2ab34ebb90d1c06c62c301c8
Source dataset
uspto-grants-1993_05
Patent number
US05212180

Reaction notes

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