Imidazole → HCID 89397429, compound

HRID 2171595Notes

Reaction equation

HRID 2171595 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([N:7]=[O:8])[C@@H:3]1[C:9]([O:11][CH3:12])=[O:10].N1C=CN=C1.[CH3:18][C:19]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])[CH3:20]>C(Cl)Cl>[Si:22]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([N:7]=[O:8])[C@@H:3]1[C:9]([O:11][CH3:12])=[O:10])([C:19]([CH3:21])([CH3:20])[CH3:18])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 89396864HCID 89396864, compound

Product 1

HCID 89397429HCID 89397429, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2S,3S)-methyl 3-hydroxy-1-nitrosopyrrolidine-2-carboxylate (13 g, 0.0742 moles) in DCM (150 mL) at room temperature were added imidazole (15.2 g, 0.224 moles) and TBDMS-Cl (22.5 g, 0.149 moles) and the mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with DCM and washed with water, brine, dried over Na2SO4 and concentrated. Purification by column chromatography over silica gel using 10% EtOAc in hexane as a solvent provided the title compound.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customPurification by column chromatography over silica gel using 10% EtOAc in hexane as a solvent

Sources & evidence

ORD record
ord-8fbd2e944adc4aac84356afac2745696
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

Loading…