Potassium Hydroxide → Tert-butyl 4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-oxopiperazine-1-carboxylate

HRID 639990Notes

Reaction equation

HRID 639990 reaction equation
Br[CH2:2][CH2:3][O:4][Si:5]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].[O:12]=[C:13]1[NH:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1.[OH-].[K+]>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Si:5]([O:4][CH2:3][CH2:2][N:18]1[CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:14][C:13]1=[O:12])([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 68638537Tert-butyl 4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-oxopiperazine-1-carboxylateYield 48.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (2-bromoethoxy)-tert-butyldimethylsilane (4.71 g, 19.7 mmol) in tetrahydrofuran (20 ml) was added dropwise at room temperature to a stirred solution of tert-butyl 3-oxopiperazine-1-carboxylate (3.94 g, 19.7 mmol), powdered potassium hydroxide (1.32 g, 23.6 mmol) and tetrabutylammonium bromide (1.27 g, 3.94 mmol) in tetrahydrofuran (30 ml) and the resulting mixture was stirred for 4 hours. The mixture was filtered and then evaporated to leave a colourless viscous oil which was purified by silica gel chromatography eluting with methyl tert-butyl ether as eluent to give tert-butyl 4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-oxopiperazine-1-carboxylate (3.42 g, 45% yield) as a colourless oil:

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customto leave a colourless viscous oil which
  4. customwas purified by silica gel chromatography
  5. washeluting with methyl tert-butyl ether as eluent

Sources & evidence

ORD record
ord-61dbb8e0478c41c58c9c5d1d25bd7fa7
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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