Methylamine → HCID 58869134, compound

HRID 2355215Notes

Reaction equation

HRID 2355215 reaction equation
[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][C@H:16]([CH2:20]OS(C4C=CC(C)=CC=4)(=O)=O)[O:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:32][NH2:33].[OH-].[Na+]>>[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][C@H:16]([CH2:20][NH:33][CH3:32])[O:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 6329Methylamine2×HCID 14798Sodium HydroxideHCID 58869190HCID 58869190, compound

Product 1

HCID 58869134HCID 58869134, compound

Conditions

Temperature
100 °C

Procedure

A solution of toluene-4-sulfonic acid (R)-7-benzenesulfonyl-chroman-2-ylmethyl ester (274 mg, 0.6 mmol) and MeNH2 (2M in THF, 5 mL) was heated at 100° C. under microwave conditions for 6 hours. MeNH2 (40% in water, 2 mL) was then added and the mixture was heated at 100° C. under microwave conditions overnight. NaOH (10%) was added and the mixture was extracted 3 times with DCM. The combined organic extracts were washed with water, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified via flash chromatography to afford the desired product (172 mg). The product was recrystallized from DCM affording 8 mg ((R)-7-benzenesulfonyl-chroman-2-ylmethyl)-methyl-amine with 79% ee and from the evaporation of the mother liquors were recovered an additional 164 mg. Recrystallation from ethanolic HCl yielded the corresponding hydrochloride salt, Mp 271.8-273.0° C.

Workup

  1. extractionthe mixture was extracted 3 times with DCM
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-d545090d7f004d9fa258dbf5f7d63216
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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