Water → 1,4,5,6,7,8-Hexahydropyrrolo[3,2-B]azepine

HRID 1839657

Reaction equation

HRID 1839657 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[N:10]O)[C:4]=2[CH:3]=[CH:2]1.CC(C[AlH]CC(C)C)C.[F-].[Na+].O>C(Cl)Cl>[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][NH:10][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 5235Sodium FluorideHCID 14487Diisobutylaluminum hydrideHCID 9156771,5,6,7-Tetrahydro-indol-4-one oxime

Product 1

HCID 225617901,4,5,6,7,8-Hexahydropyrrolo[3,2-B]azepineYield 33.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1,5,6,7-tetrahydro-indol-4-one oxime (1.2 g, 7.7 mmol) in DCM (anhydrous, 250 mL) was added DIBAL-H (1M solution in DCM, 35 mL) at 0° C. under nitrogen. After 2 hours, NaF (7 g) was added followed by water (2.24 g). After 20 mins, the reaction was filtered through celite and the solvent was removed to give 350 mg of 1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine as a brown oil

Workup

  1. waitAfter 20 mins
  2. filtrationthe reaction was filtered through celite
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-cb824d25df4649f693268d42cbe5340e
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Linked notes

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