Water → HCID 30327616, compound

HRID 1582389Notes

Reaction equation

[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([N:9]1[C:14](=O)[CH2:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][C:10]1=O)[CH2:2]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[F-].[K+]>O1CCOCC1.CCOCC>[CH2:16]([N:12]1[CH2:13][CH2:14][N:9]([C@H:3]2[CH:4]3[CH2:5][CH2:6][N:1]([CH2:8][CH2:7]3)[CH2:2]2)[CH2:10][CH2:11]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-4-benzyl-2,6-piperazinedione (1.90 g, 6.00 mmol) in 1,4-dioxane (40 mL) was added LiAlH4 (911 mg, 24.0 mmol) at room temperature under nitrogen atmosphere. The resulting suspension was stirred under reflux for 3.5 h, then cooled to 0° C. The mixture was diluted with Et2O (80 mL), then treated carefully with Na2SO410 H2O (9.1 g) and anhydrous KF (1 g). After the resulting white suspension was stirred vigorously at room temperature for 30 min, the white precipitate was removed by filtration through a pad of celite. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (NH gel, 200-350 mesh, 40 g, EtOAc) to give a product (1.39 g , 81%) as a white solid.

Workup

temperatureunder reflux for 3.5 h
stirringAfter the resulting white suspension was stirred vigorously at room temperature for 30 min
customthe white precipitate was removed by filtration through a pad of celite
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by column chromatography (NH gel, 200-350 mesh, 40 g, EtOAc)

Sources & evidence

ORD record: ord-1bc26e9b72ce44f7a927ff873421cfcf
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06734306B2

Reaction notes

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