Potassium Hydroxide → HCID 20244784, compound

HRID 2418755Notes

Reaction equation

HRID 2418755 reaction equation
[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[NH:6][C:5]1=[O:15])=[N+:2]=[N-:3].[OH-].[K+].Br[C@H:19]([CH3:27])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[N:6]([CH:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH3:27])[C:5]1=[O:15])=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 109325203-Azido-1,3,4,5-tetrahydro-2H-1-benzazepin-2-oneHCID 12882377tert-Butyl (2R)-2-bromopropanoate

Product 1

HCID 20244784HCID 20244784, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

3-Azido-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (as prepared in example 1,5 g) was added in one portion to a stirred suspension of potassium hydroxide (1.8 g) and tetrabutylammonium bromide (0.8 g) in tetrahydrofuran (50 ml) maintained at 0° under a nitrogen atmosphere. Stirring was continued for 5 minutes, then (R)-t-butyl 2-bromopropionate [J. P. Greenstein et al., J. Am. Chem. Soc. 76, 6054 (1954), H. Niedrich and G. Koller, J. Prakt. Chem. 316, 729 (1974)] (5.2 g) in tetrahydrofuran (15 ml) was added during 5 minutes. The reaction mixture was allowed to warm to room temperature while stirring for an additional 2 hours. The reaction mixture was filtered and the tetrahydrofuran removed at reduced pressure. The residue was partitioned between water (50 ml) and ether (100 ml). The organic phase was washed with 2N hydrochloric acid (10 ml), dried over magnesium sulfate, and the solvent evaporated under reduced pressure to give 3-azido-1-(1-t-butyloxycarbonylethyl)-2,3,4,5-tetrahydro-1H[1]-benzazepin-2-one as an oil that was used without further purification.

Workup

  1. temperaturemaintained at 0° under a nitrogen atmosphere
  2. stirringwhile stirring for an additional 2 hours
  3. filtrationThe reaction mixture was filtered
  4. customthe tetrahydrofuran removed at reduced pressure
  5. customThe residue was partitioned between water (50 ml) and ether (100 ml)
  6. washThe organic phase was washed with 2N hydrochloric acid (10 ml)
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-4a6e3b798bcd4f0e97bca8c967ad262b
Source dataset
uspto-grants-1984_09
Patent number
US04473575

Reaction notes

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