Hydrogen chloride-ethyl acetate → tert-butyl (1S,2R)-1-amino-7-methylindane-2-carboxylate

HRID 64428Notes

Reaction equation

HRID 64428 reaction equation
C([S@@]([NH:7][C@@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH3:17])[CH2:10][C@H:9]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=O)(C)(C)C.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[NH2:7][C@@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH3:17])[CH2:10][C@H:9]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86713440tert-butyl (1S,2R)-1-{[(S)-tert-butylsulfinyl]amino}-7-methylindane-2-carboxylate

Product 1

HCID 86713439tert-butyl (1S,2R)-1-amino-7-methylindane-2-carboxylateYield 89.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 140 mg of tert-butyl (1S,2R)-1-{[(S)-tert-butylsulfinyl]amino}-7-methylindane-2-carboxylate in 9.1 ml of ethyl acetate was added 0.88 ml of a 4 M hydrogen chloride/ethyl acetate solution, followed by stirring at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and to the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate to carry out a layer separation operation. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 88 mg of tert-butyl (1S,2R)-1-amino-7-methylindane-2-carboxylate.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionto the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate
  3. customa layer separation operation
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a622f2db1df140b3965c7e7120b30305
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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