Imidazole → HCID 57090666, compound

HRID 2258355Notes

Reaction equation

HRID 2258355 reaction equation
[CH3:1][C@@H:2]1[CH2:7][NH:6][C@@H:5]([CH3:8])[CH2:4][N:3]1[C@@H:9]([C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:23]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])([CH3:25])[CH3:24].N1C=CN=C1.O>CN(C)C=O.C(O)C.ClCCl>[Si:27]([O:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C@H:9]([N:3]2[CH2:4][C@H:5]([CH3:8])[NH:6][CH2:7][C@H:2]2[CH3:1])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:17]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:29])[CH3:28]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 56986028HCID 56986028, compound

Product 1

HCID 57090666HCID 57090666, compoundYield 61.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (±)-3-((αR*)-α-((2R*,5S*)-2,5-dimethyl-1-piperazinyl)benzyl)phenol (1.98 g, 6.7 mmol), from Example 38, tert-butylchlorodimethylsilane (1.51 g, 10.1 mmol), and imidazole (1.14 g, 16.8 mmol) in 30 mL of N,N-dimethylformamide was stirred at room temperature under nitrogen overnight. The reaction mixture was poured into cold water and extracted wtih diethyl ether. The ether extracts were dried over sodium sulfate and the solvent removed under vacuum to give a yellow oil. Chromatography on silica gel with dichloromethane:ethanol (1-7%) gave 1.68 g (61%) of (±)-(3-((αR*)-α-((2R*,5S*)-2,5-dimethyl-1-piperazinyl)-benzyl)phenyl) (tert-butyldimethylsilyl) ether as a yellow oil. NMR (CDCl3, 200 MHz): δ0.1 (s, 6H); 0.9 (s, 9H); 1.05 (d, J=6 Hz, 3H); 1.2 (d, J=6 Hz, 3H); 1.7 (t, J=10 Hz, 1H); 2.45 (br m, 1H); 2.7 (rn, 2H); 3.0 (m, 2H); 3.4 (br s, 1H); 5.25 (s, 1H); 6.7 (d,J=8 Hz, 1H); 6.9 (d, J=8 Hz, 1 H);7.05 (s, 1H); 7.1 (m, 3H); 7.3 (m, 3H).

Workup

  1. extractionextracted wtih diethyl ether
  2. dry with materialThe ether extracts were dried over sodium sulfate
  3. customthe solvent removed under vacuum
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-afec26a20ebd4f659128c508bc380dd5
Source dataset
uspto-grants-1997_08
Patent number
US05658908

Reaction notes

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