Imidazole → HCID 59201686, compound

HRID 451874Notes

Reaction equation

HRID 451874 reaction equation
[Br:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[OH:8].N1C=CN=C1.[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16].O>CN(C=O)C>[Br:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[O:8][Si:18]([C:15]([CH3:17])([CH3:16])[CH3:14])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 108669212425-33-4

Product 1

HCID 59201686HCID 59201686, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution (1R*,2R*)-2-bromocyclohexanol (27 g, 0.151 mol) of and imidazole (24.9 g, 0.366 mol) in DMF (500 mL) was added TBSCl (24.9 g, 0.166 mol), the reaction mixture was stirred overnight at rt. Water was added and extracted by EtOAc three times. The combined organic layers were dried, filtered, and concentrated to give ((1R*,2R*)-2-bromocyclohexyloxy)(tert-butyl)dimethylsilane (32 g, 72%). 1H NMR (CDCl3, 400 MHz) δ 0.05-1.05 (d, 6H), 0.90 (s, 9H), 1.20-1.40 (m, 3H), 1.60-1.85 (m, 3H), 1.98-2.10 (m, 1H), 2.25-2.40 (m, 1H), 3.63-3.73 (m, 1H), 3.85-3.97 (m, 1H).

Workup

  1. extractionextracted by EtOAc three times
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e4a9a770ef1c479bbdb5c5885cd40e01
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

Loading…