Imidazole → HCID 66783809, compound

HRID 1096291Notes

Reaction equation

HRID 1096291 reaction equation
[CH2:1]([Si:3]([CH2:7][CH3:8])([CH2:5][CH3:6])Cl)[CH3:2].[CH2:9]([O:16][C:17](=[O:32])[NH:18][CH2:19][C@@H:20]([OH:31])[CH2:21][N:22]1[CH2:29][CH2:28][C:25]2([CH2:27][CH2:26]2)[C@H:24]([OH:30])[CH2:23]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1[CH:37]=[CH:36]N=C1>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH2:9]([O:16][C:17](=[O:32])[NH:18][CH2:19][C@@H:20]([O:31][Si:3]([CH2:36][CH3:37])([CH2:5][CH3:6])[CH2:1][CH3:2])[CH2:21][N:22]1[CH2:29][CH2:28][C:25]2([CH2:27][CH2:26]2)[C@H:24]([O:30][Si:3]([CH2:7][CH3:8])([CH2:5][CH3:6])[CH2:1][CH3:2])[CH2:23]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 66783379HCID 66783379, compound

Product 1

HCID 66783809HCID 66783809, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Triethylchlorosilane (351 mg, 2.33 mmol) was added to a solution of [(R)-2-hydroxy-3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-carbamic acid benzyl ester (260 mg, 0.78 mmol), imidazole (264 mg, 3.89 mmol), and 4-(dimethylamino)pyridine (1.9 mg, 16 μmol) in N,N-dimethylformamide at RT, then after 90 min the reaction mixture was partitioned between EtOAc and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane/EtOAc 7:3) afforded the title compound (397 mg, 91%). Light yellow liquid, MS: 563.4 (M+H)+.

Workup

  1. customafter 90 min the reaction mixture was partitioned between EtOAc and sat. aq. NaHCO3 solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-6bf531b0407c42d59135a8612a2da64b
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

Loading…