Methanamine--water (1/1) → HCID 16225761, compound

HRID 2355221Notes

Reaction equation

HRID 2355221 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C@H:17]([CH2:21]OS(C)(=O)=O)[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.O.[CH3:28][NH2:29]>>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C@H:17]([CH2:21][NH:29][CH3:28])[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 13000549Methanamine--water (1/1)HCID 58869139HCID 58869139, compound

Product 1

HCID 16225761HCID 16225761, compoundYield 97%

Conditions

Temperature
100 °C

Procedure

A mixture of methanesulfonic acid (R)-7-(3-fluoro-benzenesulfonyl)-chroman-2-ylmethyl ester (1.145 g, 2.86 mmol) and methylamine hydrate (10.mL) was heated in a sealed tube at 100° C. for 24 hours. The mixture was cooled and extracted with methylene chloride. The combined organic layers were washed with water and brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (methylene chloride:MeOH 4:1) to give 0.932 g (97%) of [(R)-7-(3-fluoro-benzenesulfonyl)-chroman-2-ylmethyl]-methyl-amine. MP=259.0-261.0° C.; MS (M+H)=336.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with methylene chloride
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (methylene chloride:MeOH 4:1)

Sources & evidence

ORD record
ord-2064dab12b9b4feea5ed8aefae4497f2
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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