Imidazole → HCID 59226436, compound

HRID 1920215Notes

Reaction equation

HRID 1920215 reaction equation
[N:1]([CH:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[N+:16]([O-:18])=[O:17])[CH2:7][CH2:6][CH:5]1[OH:19])=[N+:2]=[N-:3].[CH3:20][C:21]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:1]([CH:4]1[CH:5]([O:19][Si:24]([C:21]([CH3:23])([CH3:22])[CH3:20])([CH3:26])[CH3:25])[CH2:6][CH2:7][C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[N+:16]([O-:18])=[O:17])=[CH:9]1)=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 59226607HCID 59226607, compound

Product 1

HCID 59226436HCID 59226436, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (+/−)-2-azido-4-(3-nitropyridin-4-yl)cyclohex-3-enol (1.0 equiv.) in DCM (0.15M) was added TBSCl (2.0 equiv.), imidazole (2.0 equiv.) and DMAP (0.1 equiv.) at room temperature. After 18 h, water was added, the organics were dried with brine, then Na2SO4, and concentrated. The crude material was loaded to silica gel and purified via ISCO eluting with ethyl acetate and hexanes (20%). Obtained (+/−)-4-(3-azido-4-(tert-butyldimethylsilyloxy)cyclohex-1-enyl)-3-nitropyridine as a yellow oil in 60% yield. LCMS (m/z): 376.3 (MH+), LC Rt=5.848 min.

Workup

  1. dry with materialthe organics were dried with brine
  2. concentrationNa2SO4, and concentrated
  3. custompurified via ISCO
  4. washeluting with ethyl acetate and hexanes (20%)

Sources & evidence

ORD record
ord-74b6f80635a7411ba43372876d9fd978
Source dataset
uspto-grants-2012_05
Patent number
US08168794B2

Reaction notes

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