Ammonia → HCID 18378679, compound

HRID 2298807Notes

Reaction equation

HRID 2298807 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([C:13]([N:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][CH2:18][CH2:17][CH2:16]2)=O)[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].N>O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH2:13][N:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 18378619methyl 2-methoxy-4-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonylbenzoate

Product 1

HCID 18378679HCID 18378679, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-bath-cooled solution of methyl 2-methoxy-4-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonylbenzoate (350 mg) in tetrahydrofuran (15 ml) was added dropwise a 1M solution of borane-tetrahydrofuran complex (3.1 ml), and the mixture was stirred at room temperature for 6 hours. After quenching the reaction with 1N hydrochloric acid (10 ml), the mixture was adjusted to pH 8-9 with concentrated ammonia solution and extracted with chloroform. The solution was washed with brine. The organic layer was dried over magnesium sulfate and the solvent was evaporated in vacuo. The crude product was purified by silica gel column chromatography (10% ethyl acetate in hexane) to give methyl 2-methoxy-4-(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)methylbenzoate (255 mg).

Workup

  1. customAfter quenching
  2. customthe reaction with 1N hydrochloric acid (10 ml)
  3. extractionextracted with chloroform
  4. washThe solution was washed with brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe crude product was purified by silica gel column chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2e82213cccd1447cb07cc5d645e1d182
Source dataset
uspto-grants-2002_12
Patent number
US06495542B1

Reaction notes

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