Potassium Iodide → HCID 86701815, compound

HRID 338658Notes

Reaction equation

HRID 338658 reaction equation
[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][S:2]2(=[O:9])=[O:8].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[CH2:19][CH2:20][OH:21].[I-].[K+]>C(#N)C>[OH:21][CH2:20][CH2:19][N:5]1[CH2:6][C@@H:1]2[CH2:7][C@H:4]1[CH2:3][S:2]2(=[O:9])=[O:8]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 108982-BromoethanolHCID 62657Potassium Phosphate, TribasicHCID 55299066HCID 55299066, compound

Product 1

HCID 86701815HCID 86701815, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (1S,4S)-2-thia-5-azabicyclo[2.2.1]heptane 2,2-dioxide (65 mg, 0.442 mmol), potassium phosphate (375 mg, 1.766 mmol), 2-bromoethanol (221 mg, 1.766 mmol) and potassium iodide (147 mg, 0.883 mmol) in acetonitrile (2 mL) was heated up at 120° C. for 4 hours. The reaction mixture was concentrated under reduced pressure and purified in silica gel with 0-15% methanol/ethyl acetate to provide the title product (60 mg, 71% yield) as a white solid. LCMS: m/e 192.07 (M+H)+, 0.87 min (method 2)

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified in silica gel with 0-15% methanol/ethyl acetate

Sources & evidence

ORD record
ord-e987e48de4ea4ad09d8346a89d416b8f
Source dataset
uspto-grants-2014_11
Patent number
US08889854B2

Reaction notes

Loading…