HCID 58869127, compound → HCID 58869130, compound

HRID 2355220Notes

Reaction equation

HRID 2355220 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][N:22]=[N+]=[N-])[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[H][H]>C1COCC1.[Pd]>[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][NH2:22])[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 58869127HCID 58869127, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58869130HCID 58869130, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of C—[(R)-7-(3-fluoro-benzenesulfonyl)-chroman-2-yl]-methyl azide (1.76 g, 5.07 mmol) in 30 mL of THF was added 10% Pd/C (0.176 g). The reaction mixture was hydrogenated at 1.5 atmospheric pressure of hydrogen for 18 hours. The mixture was filtered and the filtrated was evaporated under reduced pressure. The residue was purified by flash chromatography (methylene chloride/MeOH 7:3) to give 1.53 g (94%) of C—[(R)-7-(3-Fluoro-benzenesulfonyl)-chroman-2-yl]-methylamine. MP=257.1-258.9° C.; MS (M+H)=322.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrated was evaporated under reduced pressure
  3. customThe residue was purified by flash chromatography (methylene chloride/MeOH 7:3)

Sources & evidence

ORD record
ord-4008394bc6924786a946a2edefed38fe
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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