Tetrabutylammonium Fluoride → Tert-butyl 4-[4-(2-hydroxyethyl)benzyl]piperazine-1-carboxylate

HRID 1023327Notes

Reaction equation

[Si]([O:8][CH2:9][CH2:10][C:11]1[CH:30]=[CH:29][C:14]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:13][CH:12]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O.O>[OH:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:18][CH2:17]2)=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a THF (8 mL) solution of tert-butyl 4-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}-ethyl)benzyl]piperazine-1-carboxylate (0.96 g) was added 1.0 M solution of TBAF in THF (2.32 mL) at 0° C. The resultant mixture was stirred at room temperature for 2.5 hours. After cooling to 0° C., the reaction mixture was diluted with AcOEt and water. The organic layer was washed with saturated aqueous NaCl, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CH2Cl2/MeOH=40/1) to afford tert-butyl 4-[4-(2-hydroxyethyl)benzyl]piperazine-1-carboxylate (0.55 g) as a colorless oil.

Workup

washThe organic layer was washed with saturated aqueous NaCl
dry with materialdried over anhydrous MgSO4
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (CH2Cl2/MeOH=40/1)

Sources & evidence

ORD record: ord-220d01dedcfa460da7db884558a588ec
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722663B2

Reaction notes

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