Potassium Hydroxide → HCID 68881505, compound

HRID 1785140Notes

Reaction equation

HRID 1785140 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[O:13]=[C:14]1[NH:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1.[OH-].[K+]>C1COCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Si:6]([O:5][CH2:4][CH2:3][CH2:2][N:19]1[CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:15][C:14]1=[O:13])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 68881505HCID 68881505, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

(3-Bromopropoxy)-tert-butyldimethylsilane (2.53 g, 0.01 mol) in THF (10 ml) was added dropwise at room temperature to a stirred mixture of tert-butyl 3-oxopiperazine-1-carboxylate (2.0 g, 0.01 mol), powdered potassium hydroxide (0.67 g, 0.012 mol) and tetra-n-butylammonium bromide (0.63 g, 0.002 mol) in THF (15 ml). The reaction was stirred 2 hr then filtered and evaporated. The residue was purified by column chromatography on silica using ethyl acetate as eluent to give tert-butyl 4-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-3-oxopiperazine-1-carboxylate (2.98 g, 80%) as a colourless oil; NMR Spectrum:(CDCl3) 0.02 (s, 6H), 0.87 (s, 9H), 1.43 (s, 9H), 1.76 (quintet, 2H), 3.35 (m, 2H), 3.45 (t, 2H), 3.60 (m, 4H), 4.03 (s, 2H)

Workup

  1. filtrationthen filtered
  2. customevaporated
  3. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-00e317efb747458091e0f9ae55df3bc9
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

Loading…