Sodium Hydroxide → (1S,6S)-1-Amino-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-ene

HRID 1917382Notes

Reaction equation

[H-].COCCO[Al+]OCCOC.[Na+].[H-].[NH2:15][C@:16]12[CH2:24][N:23]([C@@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[C:22](=O)[C@@H:21]1[CH2:20][CH:19]=[CH:18][CH2:17]2.[OH-].[Na+]>C1(C)C=CC=CC=1>[NH2:15][C@:16]12[CH2:24][N:23]([C@@H:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH3:26])[CH2:22][C@@H:21]1[CH2:20][CH:19]=[CH:18][CH2:17]2

Participants

Conditions

Temperature: 80 °C

Procedure

A 65% solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene (2.87 mL, 9.56 mmol) was added to a solution of (1S,6R)-1-amino-7-oxo-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-ene (612 mg, 2.39 mmol) in toluene (11.9 mL), and the mixture was stirred at 80° C. for one hour. A 5 mol/L sodium hydroxide solution (15.0 mL) was added to the reaction solution with stirring under ice-cooling, followed by extraction with toluene (30 mL×2). The organic layer was washed with brine (90 ml) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give 450 mg of the title compound.

Workup

stirringwith stirring under ice-
temperaturecooling
extractionfollowed by extraction with toluene (30 mL×2)
washThe organic layer was washed with brine (90 ml)
dry with materialdried over anhydrous sodium sulfate
filtrationAfter filtration
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-63c09dcb08bb42f49e95d7b1253e081d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618094B2

Reaction notes

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