Bromine → HCID 19809490, compound

HRID 374254Notes

Reaction equation

HRID 374254 reaction equation
[C:1]([C:4]12[CH2:11][N:8]([CH2:9][CH2:10]1)[CH2:7][CH2:6][CH2:5]2)(=[O:3])[CH3:2].[Br:12]Br>CO.O>[BrH:12].[Br:12][CH2:2][C:1]([C:4]12[CH2:11][N:8]([CH2:9][CH2:10]1)[CH2:7][CH2:6][CH2:5]2)=[O:3]

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 10702020HCID 10702020, compound

Product 1

HCID 19809490HCID 19809490, compoundYield 225.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the hydrobromide salt of (±) 5-acetyl-1-azabicyclo[3.2.1]octane (D4) (2.0g; 8.5 mmole) in dry methanol (35ml) was cooled to -10° C. and treated with a solution of bromine (0.44ml; 8.5 mmole) in dry methanol (5ml). The reaction was maintained at 0° C. for 18h. A further quantity of bromine (0.44 ml) was added and after 5h at room temperature the reaction was diluted with water and stirred for 1h. Evaporation of solvent and excess reagent in vacuo afforded a yellow foam (3.0 g) consisting mainly of the title compound (D5). This material was used in the next stage without purification.

Workup

  1. customEvaporation of solvent and excess reagent in vacuo

Sources & evidence

ORD record
ord-1d5960275b064c1e9642571d5af7c411
Source dataset
uspto-grants-1992_11
Patent number
US05166357

Reaction notes

Loading…