Imidazole → HCID 86659848, compound

HRID 2402757Notes

Reaction equation

HRID 2402757 reaction equation
Br[CH:2]1[CH2:16][C@@H:5]2[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][C@@H:4]2[C:3]1=[O:17].[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1>CC(C)=O>[N:18]1([CH:2]2[CH2:16][C@@H:5]3[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][C@@H:4]3[C:3]2=[O:17])[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 86659849HCID 86659849, compound

Product 1

HCID 86659848HCID 86659848, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of (3aR,6aS)-tert-butyl 5-bromo-4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (300 mg, 0.986 mmol) from Step 1, 1H-imidazole (201 mg, 2.96 mmol), and acetone (0.5 mL) in a 4 mL vial was stirred for 1.5 h at 80° C. The reaction mixture was then concentrated. The crude product was purified chromatographically using a 12 g silica gel cartridge with a gradient of 0-10% CH3OH/CH2Cl2 over 20 min to give (3aR,6aS)-tert-butyl 5-(1H-imidazol-1-yl)-4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate: MS (ESI+) m/z 292 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customThe crude product was purified chromatographically
  3. customover 20 min

Sources & evidence

ORD record
ord-2fc83fd9c3864f768bd462fead927e3a
Source dataset
uspto-grants-2014_08
Patent number
US08796470B2

Reaction notes

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