Hydrochloric Acid → HCID 16067544, compound

HRID 2246720Notes

Reaction equation

HRID 2246720 reaction equation
C(O[C:6]([N:8](C)[CH2:9][CH2:10][C@H:11]([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:19]1=[O:32])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)(C)(C)C.Cl.C(OCC)(=O)C>C(O)C>[CH3:6][NH:8][CH2:9][CH2:10][C@H:11]([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[C:19]1=[O:32])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 68525804HCID 68525804, compound

Product 1

HCID 16067544HCID 16067544, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1′-[(1S)-3-(tert-butoxycarbonyl-methylamino)-1-phenylpropyl]spiro[cyclohexane-1,3′-indol]-2′(1′H)-one (70 mg, 0.15 mmol) was dissolved in ethanol (3 mL) and 2N HCl in ethyl acetate (0.3 mL, 0.6 mmol) was added. The mixture was stirred 16 hours then concentrated under a stream of nitrogen. The residue was purified via chromatography (silica, 5% methanol saturated with ammonia in chloroform) to give 54 mg of 1′-[(1S)-3-(methylamino)-1-phenylpropyl]spiro[cyclohexane-1,3′-indol]-2′(1′H)-one. The free base was dissolved in ether (2 mL) and treated with 1N hydrochloric acid in ether (0.16 mL, 0.16 mmol, 1 equivalent). The white precipitate was collected and dried under vacuum to give 54 mg of 1′-[(1S)-3-(methylamino)-1-phenylpropyl]spiro[cyclohexane-1,3′-indol]-2′(1′H)-one hydrochloride.

Workup

  1. concentrationthen concentrated under a stream of nitrogen
  2. customThe residue was purified via chromatography (silica, 5% methanol saturated with ammonia in chloroform)

Sources & evidence

ORD record
ord-89ebf8a56c0d44f6ba64c8d872dd3a43
Source dataset
uspto-grants-2010_03
Patent number
US07687529B2

Reaction notes

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