Acetonitrile → 3-Tetrahydrofuran-3-yl-3,8-diazabicyclo[3.2.1]octane

HRID 876214Notes

Reaction equation

HRID 876214 reaction equation
O=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5]C=CC=2)[N:3]1C1CCN(C(OC(C)(C)C)=O)CC1.BrN1[C:29](=O)[CH2:28][CH2:27][C:26]1=[O:31].[C:32](#[N:34])C>ClCCl.O>[O:31]1[CH2:26][CH2:27][CH:28]([N:34]2[CH2:5][CH:4]3[NH:3][CH:2]([CH2:10][CH2:9]3)[CH2:32]2)[CH2:29]1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 67472855tert-Butyl 4-(2-oxo-2,3-dihydro-1H-indol-1-yl)piperidine-1-carboxylate

Product 1

HCID 904140143-Tetrahydrofuran-3-yl-3,8-diazabicyclo[3.2.1]octaneYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

Tert-butyl 4-(2-oxoindolin-1-yl)piperidine-1-carboxylate (100 mg, 0.32 mmol) in ACN is cooled down to −10° C., N-bromosuccinimide (56.47 mg, 0.32 mmol) is added and stirred at −10° C. for 2 h. The reaction mixture is diluted with dichlormethane and water. The organic layer is separated, dried and concentrated. The crude product is used for the next step without further purification. Yield 99%, m/z 395 [M+H]+, rt 1.126 min, LC-MS Method Z020_S01.

Workup

  1. customThe organic layer is separated
  2. customdried
  3. concentrationconcentrated
  4. customThe crude product is used for the next step without further purification
  5. customYield 99%, m/z 395 [M+H]+, rt 1.126 min, LC-MS Method Z020_S01

Sources & evidence

ORD record
ord-da02d577f2cd441789b6783cfa870619
Source dataset
uspto-grants-2015_03
Patent number
US08987249B2

Reaction notes

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