Borane;tetrahydrofuran → HCID 178419151, compound

HRID 2361560Notes

Reaction equation

HRID 2361560 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([PH:12](=O)[C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:15][CH:14]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH3:25].O1CCCC1>O1CCCC1>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([PH:12][C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:20][CH2:21][CH2:22][CH2:23]4)=[CH:15][CH:14]=3)=[CH:10][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH3:25]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 178527032HCID 178527032, compound

Product 1

HCID 178419151HCID 178419151, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen stream, to a solution of bis[4-(pyrrolidin-1-yl)phenyl]phosphine oxide (2.50 g, 7.34 mmoL) synthesized in Example 13 in tetrahydrofuran (25 mL) was added borane-tetrahydrofuran solution (29 mL, 3.9 equivalents) at 25° C. to 30° C. over 2.4 hr. Then, silica gel (10.0 g, 22.6 equivalents) was added to the mixture, and the mixture was stirred at room temperature for 1 hr. Silica gel was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 25 g, dichloromethane) to give the title compound (0.7 g, white crystals). yield 27%. melting point 178.3° C.

Workup

  1. additionThen, silica gel (10.0 g, 22.6 equivalents) was added to the mixture
  2. customSilica gel was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel 25 g, dichloromethane)

Sources & evidence

ORD record
ord-04208f80776f4bca91f9b7d791c67747
Source dataset
uspto-grants-2014_04
Patent number
US08691718B2

Reaction notes

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