Imidazole → HCID 66783503, compound

HRID 1096280Notes

Reaction equation

HRID 1096280 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[NH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:21][CH2:20][C:17]2([CH2:19][CH2:18]2)[C@H:16]([OH:22])[CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([Si:28]([CH3:31])([CH3:30])Cl)([CH3:27])([CH3:26])[CH3:25].N1C=CN=C1>CN(C)C=O.CN(C)C1C=CN=CC=1>[CH2:1]([O:8][C:9](=[O:23])[NH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:21][CH2:20][C:17]2([CH2:18][CH2:19]2)[C@H:16]([O:22][Si:28]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:31])[CH3:30])[CH2:15]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 66783407HCID 66783407, compound

Product 1

HCID 66783503HCID 66783503, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of [3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-carbamic acid benzyl ester (examples 74/75A; 3.90 g, 12.2 mmol in N,N-dimethylformamide (50 mL) was added tert-butyl-dimethylchlorosilane (2.77 g, 18.3 mmol), imidazole (2.08 g, 30.6 mmol), and 4-(dimethylamino)pyridine (14 mg, 0.12 mmol) at RT. The reaction mixture was heated at 60° C. for 24 h, then partitioned between sat. aq. NaHCO3 solution and EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; EtOAc/MeOH 19:1) afforded the title compound (4.34 g, 82%). Light yellow oil, MS: 433.4 (M+H)+.

Workup

  1. custompartitioned between sat. aq. NaHCO3 solution and EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-501e0bd9bee347f2b64fb3981b55d413
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

Loading…