Tetrahydrofuran → (2R,5S)-1-benzyl-2,5-dimethylpiperazine

HRID 1838239Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.[CH2:12]([N:19]1[C@H:24]([CH3:25])[C:23](=O)[NH:22][C@@H:21]([CH3:27])[C:20]1=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>O>[CH2:12]([N:19]1[CH2:20][C@H:21]([CH3:27])[NH:22][CH2:23][C@H:24]1[CH3:25])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In an atmosphere of argon, 0.57 g of lithium aluminum hydride was added at 0° C. to 30 ml of THF solution containing 1.0 g of (3S,6R)-1-benzyl-3,6-dimethylpiperazine-2,5-dione, and the mixture was stirred overnight with heating under reflux. The reaction mixture was cooled to 0° C., 1.0 ml of water was added dropwise thereto and 1.0 ml of 10% aqueous sodium hydroxide was added dropwise thereto, and then the mixture was further mixed with 1.0 ml of water and stirred for 30 minutes. The precipitate was separated by filtration and washed with ethyl acetate, and the filtrate was washed with 10% aqueous potassium carbonate and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated. The residue was subjected to a silica gel column chromatography and eluted with chloroform-methanol-28% aqueous ammonia (25:1:0.1, v/v/v) to obtain 0.75 g of the title compound as a yellow oily substance.

Workup

temperaturewith heating
temperatureunder reflux
stirringstirred for 30 minutes
customThe precipitate was separated by filtration
washwashed with ethyl acetate
washthe filtrate was washed with 10% aqueous potassium carbonate and saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated
washeluted with chloroform-methanol-28% aqueous ammonia (25:1:0.1, v/v/v)

Sources & evidence

ORD record: ord-82e08a76750a4893b775c813a58a4ed4
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06673799B1

Reaction notes

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