Water → HCID 70976150, compound

HRID 455267Notes

Reaction equation

HRID 455267 reaction equation
Br[C@H:2]1[CH2:21][N:5]2[C:6](=[O:20])[N:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=3)[CH2:8][C@@H:4]2[CH2:3]1.[N-:22]=[N+:23]=[N-:24].[Na+].O>CN(C=O)C>[N:22]([C@@H:2]1[CH2:21][N:5]2[C:6](=[O:20])[N:7]([C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=3)[CH2:8][C@@H:4]2[CH2:3]1)=[N+:23]=[N-:24]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86673575HCID 86673575, compound

Product 1

HCID 70976150HCID 70976150, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

The mixture of (6R,7aS)-6-Bromo-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (example 20, step b) (1.45 g, 4 mmol) and NaN3 (0.34 g, 5.2 mmol) in DMF (50 mL) was heated to 70° C. for 1.5 h. Then to the mixture was added water (100 mL) and extracted with EtOAc (100 mL×2), the organic layer was washed water (100 mL) and brine (100 mL). The combined organic layer was evaporated to dryness and the crude product (1.0 g, 77%) was used without further purification in the next step.

Workup

  1. extractionextracted with EtOAc (100 mL×2)
  2. washthe organic layer was washed water (100 mL) and brine (100 mL)
  3. customThe combined organic layer was evaporated to dryness
  4. customthe crude product (1.0 g, 77%) was used without further purification in the next step

Sources & evidence

ORD record
ord-2e42b3c396224ae4838bdd2bef389599
Source dataset
uspto-grants-2013_07
Patent number
US08497288B2

Reaction notes

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