Imidazole → HCID 21699649, compound

HRID 1778506Notes

Reaction equation

HRID 1778506 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH:14]([OH:16])[CH2:15][CH:9]1[CH2:10][C:11](=[O:17])[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[CH3:23][C:24]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])[CH3:25]>C(Cl)Cl>[CH2:1]([N:8]1[CH:13]2[CH:14]([O:16][Si:27]([C:24]([CH3:26])([CH3:25])[CH3:23])([CH3:29])[CH3:28])[CH2:15][CH:9]1[CH2:10][C:11](=[O:17])[CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 21699645HCID 21699645, compound

Product 1

HCID 21699649HCID 21699649, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 8-benzyl-6-hydroxy-8-azabicyclo[3.2.1]octan-3-one (prepared according to the procedure reported in Journal of Heterocyclic Chemistry 1992, 29(6), 1541-4; 46.2 g, 0.2 mol, 1.0 eq) and imidazole (16.3 g, 0.24 mol, 1.2 eq) in DCM (500 mL) was added TBSCl (33.1 g, 0.22 mol, 1.1 eq) in DCM (100 mL) slowly at room temperature in 10 min, then the mixture was stirred at room temperature for 2 h, washed with water (300 mL) and brine (300 mL), the organic layer was dried over Na2SO4 and concentrated to give 8-benzyl-6-[tert-butyl(dimethyl)silyl]oxy-8-azabicyclo[3.2.1]octan-3-one 86a as a colorless oil, 62 g, yield: 90%. MS: calc'd (MH+) 232, measured (MH+) 232.

Workup

  1. customprepared
  2. washwashed with water (300 mL) and brine (300 mL)
  3. dry with materialthe organic layer was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-895852a3752643de888cd72bf00ffcf9
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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