Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-amine (+)-camphorsulfonate

HRID 2202229Notes

Reaction equation

HRID 2202229 reaction equation
[C:1]12([CH2:11][S:12]([OH:15])(=[O:14])=[O:13])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=[O:3].[F:16][C:17]1[CH:18]=[C:19]([NH2:28])[CH:20]=[C:21]2[C:25]=1[C:24]([CH3:27])([CH3:26])[CH2:23][CH2:22]2>C(OCC)(=O)C>[C:1]12([CH2:11][S:12]([OH:15])(=[O:13])=[O:14])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=[O:3].[F:16][C:17]1[CH:18]=[C:19]([NH2:28])[CH:20]=[C:21]2[C:25]=1[C:24]([CH3:26])([CH3:27])[CH2:23][CH2:22]2

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 1186227997-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-amine

Product 1

HCID 1317357327-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-amine (+)-camphorsulfonateYield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of (+)-camphorsulfonic acid (1.49 g, 6.42 mmol) in ethyl acetate (37.5 mL) was added to a solution of the crude 7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-amine in ethyl acetate (15 mL) at room temperature, and the used container was washed with ethyl acetate (7.5 mL). The mixture was stirred at 0° C. for 1 hr, and filtered, and the used filter was washed with ethyl acetate. The filtrate was concentrated under reduced pressure, ethyl acetate (60 mL) was added to the residue, and the mixture was stirred at 0° C. for 2 hr. The precipitate was collected by filtration, washed with ethyl acetate, and dried over at 40° C. to give 7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-amine (+)-camphorsulfonate (1.38 g, 3.36 mmol, 58%) as pale-yellow crystals.

Workup

  1. washthe used container was washed with ethyl acetate (7.5 mL)
  2. filtrationfiltered
  3. filtrationthe used filter
  4. washwas washed with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure, ethyl acetate (60 mL)
  6. additionwas added to the residue
  7. stirringthe mixture was stirred at 0° C. for 2 hr
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with ethyl acetate
  10. customdried over at 40° C.

Sources & evidence

ORD record
ord-d4ce6c40ef8c4bc7ac6f5fefe0170e0f
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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