Methanol → HCID 117698048, compound

HRID 1778473Notes

Reaction equation

HRID 1778473 reaction equation
[CH:1]12[NH:13][CH:5]([CH2:6][CH:7]([CH2:9][C:10]([OH:12])=[O:11])[CH2:8]1)[CH2:4][O:3][CH2:2]2.S(Cl)(Cl)(=O)=O.[CH3:19]O>>[CH3:19][O:11][C:10](=[O:12])[CH2:9][CH:7]1[CH2:6][CH:5]2[NH:13][CH:1]([CH2:2][O:3][CH2:4]2)[CH2:8]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24648Sulfuryl chlorideHCID 73977857HCID 73977857, compound

Product 1

HCID 117698048HCID 117698048, compoundYield 99%

Procedure

To a solution of (3-oxa-9-aza-bicyclo[3.3.1]non-7-yl)-acetic acid (200 mg, 0.9 mmol) in 10 mL of methanol was added dropwise sulfuryl chloride (0.3 mL, 1.8 mmol) under ice cooling. After the mixture was refluxed for 3 hours, it was concentrated in vacuo. The residue was extracted with ethyl acetate (20 mL×2). The organic layer was washed with saturated aqueous sodium bicarbonate solution (20 mL×2), and then dried over anhydrous sodium sulfate and then concentrated in vacuo to afford (3-oxa-9-aza-bicyclo[3.3.1]non-7-yl)-acetic acid methyl ester (Compound AG) as colorless oil (179 mg, 99%) which was used directly in next step without further purification. MS: calc'd (MH+) 200, measured (MH+) 200.

Workup

  1. temperatureAfter the mixture was refluxed for 3 hours
  2. concentrationit was concentrated in vacuo
  3. extractionThe residue was extracted with ethyl acetate (20 mL×2)
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (20 mL×2)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d910f7c4f43e47b880f63d8d854db511
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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