9-Borabicyclo(3.3.1)nonane → 4-(3-(9-Borabicyclo[3.3.1]nonan-9-yl)propyl)morpholine

HRID 2364605Notes

Reaction equation

HRID 2364605 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3].[BH:10]1[CH:15]2[CH2:16][CH2:17][CH2:18][CH:11]1[CH2:12][CH2:13][CH2:14]2>C1COCC1>[CH:11]12[B:10]([CH2:3][CH2:2][CH2:1][N:4]3[CH2:9][CH2:8][O:7][CH2:6][CH2:5]3)[CH:15]([CH2:16][CH2:17][CH2:18]1)[CH2:14][CH2:13][CH2:12]2

Participants

4

Reactant 2

HCID 789669-Borabicyclo(3.3.1)nonaneHCID 136522Allylmorpholine

Product 1

HCID 669614874-(3-(9-Borabicyclo[3.3.1]nonan-9-yl)propyl)morpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-allylmorpholine (2.54 g, 20 mmol) in THF (40 mL) was added 9-BBN (2.44 g, 10 mmol). The reaction mixture was refluxed until the reaction was complete. After cooling to room temperature, the mixture was concentrated under reduced pressure to give the crude 4-(3-(9-borabicyclo[3.3.1]nonan-9-yl)propyl)morpholine that was used directly without further purification. LCMS ESI (+) m/z 250 (M+1) detected.

Workup

  1. temperatureThe reaction mixture was refluxed until the reaction
  2. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4bf6dea729ad40f5988bb89d6a15541d
Source dataset
uspto-grants-2014_04
Patent number
US08691809B2

Reaction notes

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