Imidazole → HCID 57090666, compound

HRID 1460121Notes

Reaction equation

HRID 1460121 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 with 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 (m, 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, 1H); 7.05 (s, 1H); 7.1 (m, 3H); 7.3 (m, 3H).

Workup

  1. extractionextracted with 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-7d405ff86ddb4b5099b11376cfd006ed
Source dataset
uspto-grants-1998_12
Patent number
US05854249

Reaction notes

Loading…